Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A
Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a coc...
Saved in:
| Published in | Organic letters Vol. 18; no. 13; pp. 3210 - 3213 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.07.2016
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1523-7060 1523-7052 1523-7052 |
| DOI | 10.1021/acs.orglett.6b01431 |
Cover
Loading…
| Abstract | Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates. Under the optimized conditions, competing proto-destannation is marginal; the method proved compatible with various (acid sensitive) functional groups and was applied to a short formal total synthesis of the antibiotic tubelactomicin A. |
|---|---|
| AbstractList | Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates. Under the optimized conditions, competing proto-destannation is marginal; the method proved compatible with various (acid sensitive) functional groups and was applied to a short formal total synthesis of the antibiotic tubelactomicin A. Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)₂ and Ph₃As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates. Under the optimized conditions, competing proto-destannation is marginal; the method proved compatible with various (acid sensitive) functional groups and was applied to a short formal total synthesis of the antibiotic tubelactomicin A. Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates. Under the optimized conditions, competing proto-destannation is marginal; the method proved compatible with various (acid sensitive) functional groups and was applied to a short formal total synthesis of the antibiotic tubelactomicin A.Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates. Under the optimized conditions, competing proto-destannation is marginal; the method proved compatible with various (acid sensitive) functional groups and was applied to a short formal total synthesis of the antibiotic tubelactomicin A. Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under a CO atmosphere; key to success is the use of 1,4-benzoquinone as a stoichiometric oxidant in combination with trifluoroacetic acid as a cocatalyst. The acid lowers the LUMO of the quinone and likely marshals the critical assembly of the substrates. Under the optimized conditions, competing proto-destannation is marginal; the method proved compatible with various (acid sensitive) functional groups and was applied to a short formal total synthesis of the antibiotic tubelactomicin A. |
| Author | Fürstner, Alois Sommer, Heiko |
| AuthorAffiliation | Max-Planck-Institut für Kohlenforschung |
| AuthorAffiliation_xml | – name: Max-Planck-Institut für Kohlenforschung |
| Author_xml | – sequence: 1 givenname: Heiko surname: Sommer fullname: Sommer, Heiko – sequence: 2 givenname: Alois surname: Fürstner fullname: Fürstner, Alois email: fuerstner@kofo.mpg.de |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27280547$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNkktv1TAQhSNURB_wC5BQlkgot34ktcPuKtAWqRILyjqynQm4OHawnVuy46fj26R3wYKy8oznfEfy-JxmR9ZZyLLXGG0wIvhcqLBx_puBGDcXEuGS4mfZCa4ILRiqyNGhvkDH2WkIdwjhdFO_yI4JIxxVJTvJfl_PnXe_ZlNsQ9AhQpc3wktnZyOidjZ3fb41PyD1Udv8A3i9S4MdhPep2YFx4wA25sJ2-XYcjVYLFl0u8kvnB2HyL7ON3yG5781uJwlGqOgGrZLh9mX2vBcmwKv1PMu-Xn68ba6Lm89Xn5rtTSEo47EgksuywyVGlNRcSEYJqRlTXAnOeHqYglLUdVXVJe3qviK8IiBlCbUUTPaEnmVvF9_Ru58ThNgOOigwRlhwU2gJIogzxEv8pBTzh2VXZO_6ZpVOcoCuHb0ehJ_bxwUnwbtFcA_S9UFpsAoOMoQQZXVZVTRVJU1q_v_qRseHXTdusjGhdEGVdyF46A8YRu0-L23KS7vmpV3zkqj6L0qtrtELbZ5gzxd2P7xzk7fp__5J_AE1dtil |
| CitedBy_id | crossref_primary_10_1016_j_ccr_2017_09_003 crossref_primary_10_1021_jacs_1c08040 crossref_primary_10_1038_s41467_018_06018_2 crossref_primary_10_1002_chem_201801344 crossref_primary_10_1002_anie_202015243 crossref_primary_10_1002_chem_202101901 crossref_primary_10_1021_acscatal_9b00482 crossref_primary_10_1002_chem_201702470 crossref_primary_10_1021_acs_joc_7b02871 crossref_primary_10_1021_jacs_8b09782 crossref_primary_10_1002_ange_201812096 crossref_primary_10_1002_chin_201646060 crossref_primary_10_1070_RCR4902 crossref_primary_10_1002_ange_202305445 crossref_primary_10_1002_cjoc_202000044 crossref_primary_10_1021_jacs_8b12185 crossref_primary_10_1021_acs_orglett_3c00327 crossref_primary_10_1002_ange_201701391 crossref_primary_10_1002_chem_201605444 crossref_primary_10_1021_jacs_2c12529 crossref_primary_10_1002_ange_201700342 crossref_primary_10_1021_jacs_8b00665 crossref_primary_10_1002_chem_201705550 crossref_primary_10_1002_chem_201804988 crossref_primary_10_1002_chem_201804987 crossref_primary_10_1002_ange_202015243 crossref_primary_10_1021_acs_joc_0c01177 crossref_primary_10_1021_acs_accounts_0c00759 crossref_primary_10_1002_anie_201700342 crossref_primary_10_1002_ejoc_202300615 crossref_primary_10_1002_anie_201812096 crossref_primary_10_3390_reactions4010002 crossref_primary_10_1002_chem_201902228 crossref_primary_10_1002_anie_201701391 crossref_primary_10_1002_anie_202305445 crossref_primary_10_1021_jacs_6b12517 |
| Cites_doi | 10.1021/om00029a040 10.1055/s-1993-22368 10.1002/ejoc.201403429 10.1016/j.tetlet.2007.10.002 10.1021/ja00373a019 10.1016/S0040-4039(00)61976-7 10.1016/0040-4039(94)02362-F 10.1021/cr9703360 10.1021/jo0708442 10.1002/anie.201402719 10.1002/anie.201205946 10.1016/0040-4039(91)80222-R 10.1021/ol800137f 10.1016/0040-4020(95)00086-N 10.1002/anie.201506075 10.1039/b508524a 10.7164/antibiotics.53.1096 10.7164/antibiotics.53.1102 10.1002/anie.201006292 10.1002/anie.200500368 10.1021/ja034833b 10.1016/j.tetlet.2006.01.140 10.1021/ja00837a034 10.1021/ja051486s 10.1021/ja00025a025 10.1002/0471264180.or050.01 10.1002/adsc.200900836 10.1002/chem.201201494 10.1021/om00047a077 10.1021/ol050763x 10.1021/ar00093a004 10.1002/anie.201307584 10.1246/bcsj.74.1343 10.1021/jacs.5b01475 10.1002/anie.201311080 10.1002/0471264180.or064.03 10.1002/anie.201501608 10.1021/ja01022a040 10.1002/3527601899 10.1246/bcsj.20150317 10.1021/jo401284c 10.1002/anie.200460864 |
| ContentType | Journal Article |
| Copyright | Copyright © 2016 American Chemical Society |
| Copyright_xml | – notice: Copyright © 2016 American Chemical Society |
| DBID | AAYXX CITATION 17B 1KM 1KN BLEPL DTL EGQ GYFQL NPM 7X8 7S9 L.6 |
| DOI | 10.1021/acs.orglett.6b01431 |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2016 PubMed MEDLINE - Academic AGRICOLA AGRICOLA - Academic |
| DatabaseTitle | CrossRef Web of Science PubMed MEDLINE - Academic AGRICOLA AGRICOLA - Academic |
| DatabaseTitleList | PubMed Web of Science AGRICOLA MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KN name: Current Chemical Reactions url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.CCR sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1523-7052 |
| EndPage | 3213 |
| ExternalDocumentID | 27280547 000379455300043 10_1021_acs_orglett_6b01431 c38953427 |
| Genre | Research Support, Non-U.S. Gov't Journal Article |
| GrantInformation_xml | – fundername: MPG; Max Planck Society |
| GroupedDBID | - .K2 123 53G 55A 5VS 7~N AABXI ABFLS ABMVS ABPTK ABUCX ACGFS ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 DZ EBS ED ED~ F5P GNL IH9 IHE JG JG~ K2 P2P RNS ROL TN5 UI2 VF5 VG9 W1F X YNT --- -DZ -~X 4.4 6P2 AAHBH AAYXX ABBLG ABJNI ABLBI ABQRX ADHLV AHGAQ CITATION CUPRZ GGK 17B 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE NPM 7X8 7S9 L.6 |
| ID | FETCH-LOGICAL-a378t-2b8b4d14103298ab7322977c8ca878011ce4a9955943d9f52852ebb4e9ba7bf23 |
| IEDL.DBID | ACS |
| ISICitedReferencesCount | 32 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000379455300043 |
| ISSN | 1523-7060 1523-7052 |
| IngestDate | Fri Jul 11 10:33:38 EDT 2025 Fri Jul 11 09:36:05 EDT 2025 Thu Jan 02 23:10:15 EST 2025 Wed Jun 18 05:45:48 EDT 2025 Fri Aug 29 15:39:12 EDT 2025 Tue Jul 01 03:08:05 EDT 2025 Thu Apr 24 22:51:12 EDT 2025 Thu Aug 27 13:42:08 EDT 2020 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 13 |
| Keywords | PALLADIUM KETONES CATALYSIS ALKOXYCARBONYLATION CARBAMOYLATION COMPLEXES ALDEHYDES INTERNAL ALKYNES TRANS-HYDROGENATION NOCARDIA SP |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-a378t-2b8b4d14103298ab7322977c8ca878011ce4a9955943d9f52852ebb4e9ba7bf23 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| PMID | 27280547 |
| PQID | 1801431522 |
| PQPubID | 23479 |
| PageCount | 4 |
| ParticipantIDs | pubmed_primary_27280547 crossref_citationtrail_10_1021_acs_orglett_6b01431 webofscience_primary_000379455300043 webofscience_primary_000379455300043CitationCount acs_journals_10_1021_acs_orglett_6b01431 crossref_primary_10_1021_acs_orglett_6b01431 proquest_miscellaneous_2020870841 proquest_miscellaneous_1801431522 |
| ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 20160701 2016-07-01 |
| PublicationDateYYYYMMDD | 2016-07-01 |
| PublicationDate_xml | – month: 07 year: 2016 text: 20160701 day: 01 |
| PublicationDecade | 2010 |
| PublicationPlace | WASHINGTON |
| PublicationPlace_xml | – name: WASHINGTON – name: United States |
| PublicationTitle | Organic letters |
| PublicationTitleAbbrev | ORG LETT |
| PublicationTitleAlternate | Org. Lett |
| PublicationYear | 2016 |
| Publisher | American Chemical Society Amer Chemical Soc |
| Publisher_xml | – name: American Chemical Society – name: Amer Chemical Soc |
| References | ref9/cit9 ref17/cit17b Davies A. G. (ref4/cit4a) 2004 ref17/cit17a ref23/cit23a ref11/cit11 ref23/cit23b ref13/cit13a ref8/cit8a ref13/cit13b ref8/cit8c ref8/cit8b ref21/cit21b ref21/cit21a ref5/cit5 ref2/cit2 ref1/cit1a ref1/cit1b ref10/cit10 ref6/cit6d ref18/cit18b ref18/cit18c ref18/cit18a ref14/cit14a ref19/cit19 ref12/cit12 ref14/cit14b ref3/cit3b ref22/cit22a ref3/cit3c ref3/cit3a ref3/cit3d ref20/cit20a ref22/cit22b ref7/cit7b ref20/cit20b ref7/cit7a ref6/cit6a ref6/cit6b ref24/cit24 Pereyre M. (ref4/cit4b) 1986 ref6/cit6c Takai, K (000379455300043.39) 2004; 64 Deng, YQ (WOS:000308313100001) 2012; 18 Rummelt, SM (WOS:000337176800009) 2014; 53 Leutzsch, M (WOS:000363397300032) 2015; 54 Hegedus, L. S. (000379455300043.21) 1982; 104 Motozaki, T (WOS:000229420400047) 2005; 7 Furstner, A (WOS:000079930300003) 1999; 99 Nicolaou, KC (WOS:000226994000005) 2005; 44 Frihed, TG (WOS:000370397000001) 2016; 89 BALAS, L (WOS:A1991ER63000077) 1991; 10 Radkowski, K (WOS:000312940700065) 2013; 52 Rummelt, SM (WOS:000354260000022) 2015; 54 Rummelt, SM (WOS:000353931500043) 2015; 137 Fujiwara, S. (000379455300043.14) 2015; 2015 Hosokawa, S (WOS:000236256300036) 2006; 47 CLIFF, MD (WOS:A1995QF02200033) 1995; 36 GRENNBERG, H (WOS:A1993LC84100040) 1993; 12 HENRY, PM (WOS:A1968A835900004) 1968 Hayes, AM (WOS:000229244600028) 2005; 127 Dixon, S (WOS:000231365900015) 2005 Fujihara, T (WOS:000286729300035) 2011; 50 Farina, V. (000379455300043.12) 1997; 50 JOUSSEAUME, B (WOS:A1993KM50400008) 1993 FARINA, V (WOS:A1991GT65500025) 1991; 113 Yamamoto, Y (WOS:000275235800031) 2010; 352 Furstner, A (WOS:000340523500005) 2014; 53 BROWN, CA (WOS:A1975V652800034) 1975; 97 Anzo, T (WOS:000251621900009) 2007; 48 Chung, LW (WOS:000185711100040) 2003; 125 Fang, ZJ (WOS:000330159300037) 2013; 78 HODGSON, DM (WOS:A1995QN98200025) 1995; 51 Igarashi, M (WOS:000090088200011) 2000; 53 Sundararaju, B (WOS:000328531100028) 2013; 52 Davies, A. G. (000379455300043.7) 2004 Igarashi, M (WOS:000090088200012) 2000; 53 Sawamura, K (WOS:000248344400025) 2007; 72 HECK, RF (WOS:A1968B835100040) 1968; 90 Wu, Y (WOS:000254908000008) 2008; 10 Pereyre, M. (000379455300043.32) 1986 Ohe, T (WOS:000170518400021) 2001; 74 TAKEDA, T (WOS:A1991GQ50600028) 1991; 32 BACKVALL, JE (WOS:A1983RG20100005) 1983; 16 |
| References_xml | – ident: ref13/cit13a doi: 10.1021/om00029a040 – ident: ref6/cit6b doi: 10.1055/s-1993-22368 – volume-title: Tin in Organic Synthesis year: 1986 ident: ref4/cit4b – ident: ref6/cit6d doi: 10.1002/ejoc.201403429 – ident: ref18/cit18b doi: 10.1016/j.tetlet.2007.10.002 – ident: ref13/cit13b doi: 10.1021/ja00373a019 – ident: ref8/cit8c doi: 10.1016/S0040-4039(00)61976-7 – ident: ref22/cit22b doi: 10.1016/0040-4039(94)02362-F – ident: ref23/cit23b doi: 10.1021/cr9703360 – ident: ref18/cit18a doi: 10.1021/jo0708442 – ident: ref3/cit3d doi: 10.1002/anie.201402719 – ident: ref3/cit3c doi: 10.1002/anie.201205946 – ident: ref9/cit9 doi: 10.1016/0040-4039(91)80222-R – ident: ref20/cit20a doi: 10.1021/ol800137f – ident: ref22/cit22a doi: 10.1016/0040-4020(95)00086-N – ident: ref3/cit3b doi: 10.1002/anie.201506075 – ident: ref6/cit6c doi: 10.1039/b508524a – ident: ref17/cit17a doi: 10.7164/antibiotics.53.1096 – ident: ref17/cit17b doi: 10.7164/antibiotics.53.1102 – ident: ref24/cit24 doi: 10.1002/anie.201006292 – ident: ref7/cit7b doi: 10.1002/anie.200500368 – ident: ref3/cit3a doi: 10.1021/ja034833b – ident: ref18/cit18c doi: 10.1016/j.tetlet.2006.01.140 – ident: ref20/cit20b doi: 10.1021/ja00837a034 – ident: ref21/cit21b doi: 10.1021/ja051486s – ident: ref11/cit11 doi: 10.1021/ja00025a025 – ident: ref7/cit7a doi: 10.1002/0471264180.or050.01 – ident: ref10/cit10 doi: 10.1002/adsc.200900836 – ident: ref14/cit14a doi: 10.1002/chem.201201494 – ident: ref6/cit6a doi: 10.1021/om00047a077 – ident: ref19/cit19 doi: 10.1021/ol050763x – ident: ref14/cit14b doi: 10.1021/ar00093a004 – ident: ref12/cit12 doi: 10.1002/anie.201307584 – ident: ref8/cit8a doi: 10.1246/bcsj.74.1343 – ident: ref1/cit1a doi: 10.1021/jacs.5b01475 – ident: ref1/cit1b doi: 10.1002/anie.201311080 – ident: ref23/cit23a doi: 10.1002/0471264180.or064.03 – ident: ref5/cit5 doi: 10.1002/anie.201501608 – ident: ref8/cit8b doi: 10.1021/ja01022a040 – volume-title: Organotin Chemistry year: 2004 ident: ref4/cit4a doi: 10.1002/3527601899 – ident: ref2/cit2 doi: 10.1246/bcsj.20150317 – ident: ref21/cit21a doi: 10.1021/jo401284c – start-page: 2285 year: 1968 ident: WOS:A1968A835900004 article-title: A NEW SYNTHESIS OF CARBOXYLIC ACIDS BY A PD(2)-CATALYZED CARBON MONOXIDE INSERTION publication-title: TETRAHEDRON LETTERS – volume: 48 start-page: 8442 year: 2007 ident: WOS:000251621900009 article-title: Formal synthesis of tubelactomicins via a transannular Diels-Alder approach publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2007.10.002 – volume: 53 start-page: 3626 year: 2014 ident: WOS:000337176800009 article-title: Ruthenium-Catalyzed trans-Selective Hydrostannation of Alkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201311080 – volume: 44 start-page: 1012 year: 2005 ident: WOS:000226994000005 article-title: Chasing molecules that were never there: Misassigned natural products and the role of chemical synthesis in modern structure elucidation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200460864 – volume: 54 start-page: 12431 year: 2015 ident: WOS:000363397300032 article-title: Formation of Ruthenium Carbenes by gem-Hydrogen Transfer to Internal Alkynes: Implications for Alkyne trans-Hydrogenation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201506075 – volume: 78 start-page: 8594 year: 2013 ident: WOS:000330159300037 article-title: Asymmetric Transfer Hydrogenation of Functionalized Acetylenic Ketones publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo401284c – volume: 64 start-page: 253 year: 2004 ident: 000379455300043.39 article-title: Addition of organochromium reagents to carbonyl compounds publication-title: Org. React – volume: 12 start-page: 1790 year: 1993 ident: WOS:A1993LC84100040 article-title: ACID-INDUCED TRANSFORMATION OF PALLADIUM(0) BENZOQUINONE COMPLEXES TO PALLADIUM(II) AND HYDROQUINONE publication-title: ORGANOMETALLICS – volume: 51 start-page: 3713 year: 1995 ident: WOS:A1995QN98200025 article-title: SCOPE OF THE CHROMIUM(II)-MEDIATED SYNTHESIS OF E-ALKENYLSTANNANES FROM ALDEHYDES AND BU(3)SNCHBR(2) publication-title: TETRAHEDRON – volume: 53 start-page: 1102 year: 2000 ident: WOS:000090088200012 article-title: Tubelactomicin A, a novel 16-membered lactone antibiotic, from Nocardia sp. II. Structure elucidation publication-title: JOURNAL OF ANTIBIOTICS – volume: 90 start-page: 5546 year: 1968 ident: WOS:A1968B835100040 article-title: A SYNTHESIS OF DIARYL KETONES FROM ARYLMERCURIC SALTS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – year: 2004 ident: 000379455300043.7 publication-title: Organotin Chemistry – start-page: 117 year: 1993 ident: WOS:A1993KM50400008 article-title: 3(OR 5)-FORMYL-2-FURAN(OR PYRROLE)CARBOXYLATES AND 3(4 OR 5)-FORMYL-2-FURAN(OR PYRROLE)-CARBOXAMIDES VIA ALKOXYCARBONYLATION OR CARBAMOYLATION OF STANNYLATED FORMYL HETEROCYCLES publication-title: SYNLETT – volume: 127 start-page: 7318 year: 2005 ident: WOS:000229244600028 article-title: A class of ruthenium(II) catalyst for asymmetric transfer hydrogenations of ketones publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – start-page: 4303 year: 2005 ident: WOS:000231365900015 article-title: Zirconium mediated total synthesis of crinitol, 9-hydroxyfarnesoic acid, 9-hydroxyfarnesol, 9-hydroxysargaquinone and the selectively-protected aglycone of moritoside and euplexide A publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b508524a – volume: 89 start-page: 135 year: 2016 ident: WOS:000370397000001 article-title: Progress in the trans-Reduction and trans-Hydrometalation of Internal Alkynes. Applications to Natural Product Synthesis publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN doi: 10.1246/bcsj.20150317 – volume: 99 start-page: 991 year: 1999 ident: WOS:000079930300003 article-title: Carbon-carbon bond formations involving organochromium(III) reagents publication-title: CHEMICAL REVIEWS – volume: 36 start-page: 763 year: 1995 ident: WOS:A1995QF02200033 article-title: DIRECT SYNTHESIS OF TRIMETHYLVINYLSTANNANES FROM ALDEHYDES publication-title: TETRAHEDRON LETTERS – volume: 74 start-page: 1343 year: 2001 ident: WOS:000170518400021 article-title: Palladium(II)- and rhodium(III)-catalyzed carbonylation reaction of aryltin compounds publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN – volume: 125 start-page: 11578 year: 2003 ident: WOS:000185711100040 article-title: A theoretical study on the mechanism, regiochemistry, and stereochemistry of hydrosilylation catalyzed by cationic ruthenium complexes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034833b – volume: 52 start-page: 355 year: 2013 ident: WOS:000312940700065 article-title: A Functional-Group-Tolerant Catalytic trans Hydrogenation of Alkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201205946 – volume: 16 start-page: 335 year: 1983 ident: WOS:A1983RG20100005 article-title: PALLADIUM IN SOME SELECTIVE OXIDATION REACTIONS publication-title: ACCOUNTS OF CHEMICAL RESEARCH – volume: 50 start-page: 523 year: 2011 ident: WOS:000286729300035 article-title: Copper-Catalyzed Hydrocarboxylation of Alkynes Using Carbon Dioxide and Hydrosilanes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201006292 – volume: 10 start-page: 1533 year: 2008 ident: WOS:000254908000008 article-title: Total synthesis of (+)-brefeldin A publication-title: ORGANIC LETTERS doi: 10.1021/ol800137f – volume: 137 start-page: 5506 year: 2015 ident: WOS:000353931500043 article-title: Interligand Interactions Dictate the Regioselectivity of trans-Hydrometalations and Related Reactions Catalyzed by [Cp*RuCl]. Hydrogen Bonding to a Chloride Ligand as a Steering Principle in Catalysis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.5b01475 – volume: 54 start-page: 6241 year: 2015 ident: WOS:000354260000022 article-title: Selective Formation of a Trisubstituted Alkene Motif by trans-Hydrostannation/Stille Coupling: Application to the Total Synthesis and Late-Stage Modification of 5,6-DihydrocineromycinB publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201501608 – volume: 352 start-page: 478 year: 2010 ident: WOS:000275235800031 article-title: The First General and Selective Palladium(II)-Catalyzed Alkoxycarbonylation of Arylboronates: Interplay among Benzoquinone-Ligated Palladium(0) Complex, Organoboron, and Alcohol Solvent publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200900836 – volume: 2015 start-page: 1264 year: 2015 ident: 000379455300043.14 publication-title: Eur. J. Org. Chem. – volume: 72 start-page: 6143 year: 2007 ident: WOS:000248344400025 article-title: Total syntheses of natural tubelactomicins B, D, and E: Establishment of their stereochemistries publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0708442 – volume: 53 start-page: 1096 year: 2000 ident: WOS:000090088200011 article-title: Tubelactomicin A, a novel 16-membered lactone antibiotic, from Nocardia sp. I. Taxonomy, production, isolation and biological properties publication-title: JOURNAL OF ANTIBIOTICS – volume: 113 start-page: 9585 year: 1991 ident: WOS:A1991GT65500025 article-title: LARGE RATE ACCELERATIONS IN THE STILLE REACTION WITH TRI-2-FURYLPHOSPHINE AND TRIPHENYLARSINE AS PALLADIUM LIGANDS - MECHANISTIC AND SYNTHETIC IMPLICATIONS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 52 start-page: 14050 year: 2013 ident: WOS:000328531100028 article-title: A trans-Selective Hydroboration of Internal Alkynes publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201307584 – year: 1986 ident: 000379455300043.32 publication-title: Tin in Organic Synthesis – volume: 47 start-page: 2439 year: 2006 ident: WOS:000236256300036 article-title: Total synthesis of an antitubercular lactone antibiotic, (+)-tubelactomicin A publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2006.01.140 – volume: 18 start-page: 11498 year: 2012 ident: WOS:000308313100001 article-title: Palladium-Catalyzed Oxidative Carbocyclizations publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201201494 – volume: 104 start-page: 2444 year: 1982 ident: 000379455300043.21 publication-title: J. Am. Chem. Soc. – volume: 97 start-page: 891 year: 1975 ident: WOS:A1975V652800034 article-title: SALINE HYDRIDES AND SUPERBASES IN ORGANIC REACTIONS .9. ACETYLENE ZIPPER - EXCEPTIONALLY FACILE CONTRATHERMODYNAMIC MULTIPOSITIONAL ISOMERIZATION OF ALKYNES WITH POTASSIUM 3-AMINOPROPYLAMIDE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 10 start-page: 366 year: 1991 ident: WOS:A1991ER63000077 article-title: PALLADIUM-CATALYZED CARBAMOYLATION AND ALKOXYCARBONYLATION OF VINYLORGANOTINS AND ARYLORGANOTINS - AN EASY ENTRY INTO VINYL OR ARYL AMIDES AND ESTERS publication-title: ORGANOMETALLICS – volume: 53 start-page: 8587 year: 2014 ident: WOS:000340523500005 article-title: Catalysis for Total Synthesis: A Personal Account publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201402719 – volume: 7 start-page: 2265 year: 2005 ident: WOS:000229420400047 article-title: Total synthesis of (+)-tubelactomicin A. 2. Synthesis of the upper-half segment and completion of the total synthesis publication-title: ORGANIC LETTERS doi: 10.1021/ol050763x – volume: 32 start-page: 6563 year: 1991 ident: WOS:A1991GQ50600028 article-title: THE FRIEDEL-CRAFTS REACTION OF 1-(PHENYLTHIO)VINYL CHLORIDES publication-title: TETRAHEDRON LETTERS – volume: 50 start-page: 1 year: 1997 ident: 000379455300043.12 article-title: The Stille reaction publication-title: Org. React |
| SSID | ssj0011529 |
| Score | 2.3541722 |
| Snippet | Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under... Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)(2) and Ph3As in MeOH... Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)2 and Ph3As in MeOH under... Alkenyltin derivatives flanked by a hydroxyl group are subject to methoxycarbonylation when treated with catalytic amounts of Pd(OAc)₂ and Ph₃As in MeOH under... |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref acs |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 3210 |
| SubjectTerms | antibiotics benzoquinones chemical reactions Chemistry Chemistry, Organic methanol moieties oxidants Physical Sciences Science & Technology |
| Title | Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A |
| URI | http://dx.doi.org/10.1021/acs.orglett.6b01431 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000379455300043 https://www.ncbi.nlm.nih.gov/pubmed/27280547 https://www.proquest.com/docview/1801431522 https://www.proquest.com/docview/2020870841 |
| Volume | 18 |
| WOS | 000379455300043 |
| WOSCitedRecordID | wos000379455300043 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV1LT-MwELYQe4DLPngsZdmVV-qBAy6NYyfx3qrsVhXScqFI3CLbcSRESBFNV4ITP52ZPEqXQtVjEj_i8TjzOTP-hpBuP-hnHHA1085IJnSmmPZsnwkhU-cLYwKHvwb-ngejS3F2Ja8WDqu_8uBz71TbKV7DKMpeYJCODjY7H3gAyxiRUHwxdxqAKVIVPSr3GZLCtCRDbzeC5shO_zdHSxjzTXNUmZ7hJ3LeHuCpI05uerPS9OzjMp_jeqP6TD42IJQOaq35QjZcsUO24jb32y55Gj2k2FvOYPpQEVIa63uDUezVTNJJRgf5jYPr8rqgv0GN_1UM4tNfdCEMieoipYMXFzktJ1TTIcLknF48FAA-oXVsbDwzLsfUP7fo6aeDPXI5_DOOR6zJ1cC0H0Yl4yYyIsWgUZ-rSJsQPhQALW1kdRSCFfSsE1oh3Z3wU5VJHknujBFOGR2ajPv7ZLOYFO6A0EAqbaQCmwqmU4YWNmQ8UBp2ojwTVtgOOQbpJc1amyaVG517Cd5sRJo0Iu0Q3s5uYhvOc0y9ka-udDKvdFdTfqwu_rNVmwRmCf0tunCTGbxYVBUAhPt-GY5JUsN-JKCdr7XOzTvlmDpMirBDuotKOH9ekQcpgYmf0KHbId46xeJGDsh5UB6uL8tvZBvAYlCHKh-RzfJ-5r4DICvNj2oZPgNV4zH_ |
| linkProvider | American Chemical Society |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1Lb9QwELZQOZQL78eWl5F64ICXjWMnMbcosFqg7aW7Um-R7ThS1ZBFTbZSOfHTmfF60wKlKsck9sQZTzKfM-NvCNmdJJOaA65m2hnJhK4V05GdMCFk5WJhTOLw18D-QTJbiC9H8ihsCsO9MDCIDiR1Poh_wS4QvQ_n4GH6cWKQlQ7WPLcBjnC067w4HGIH4JGUZ0nlMUNumA3X0NVC0CvZ7nev9BfUvNIreQ80vUcWw9h94snJeNWbsf3xB63j_z7cfXI3QFKar23oAbnl2odku9hUgntEfs7OK7xpw2Ay0SwqWuhTgzntfl7psqZ5c-LguD9u6Ucw6jPPJ959oJeSkqhuK5pfBMxpv6SaThE0N_TwvAUoCtJR2HxlXIOFgL5h3J_mj8li-mlezFio3MB0nGY94yYzosIU0pirTJsUPhsANG1mdZaCT4ysE1oh-Z2IK1VLnknujBFOGZ2amsdPyFa7bN0zQhOptJEKPCw4UplaWJ7xRGlYl_JaWGFH5C1orwxvXlf6oDqPSjwZVFoGlY4I30xyaQMDOhbiaK7v9G7o9H1NAHJ98zcb6ylhljD6olu3XMHAMt8A8O6_23AsmZpOMgFynq5Nb7gpx0JiUqQjsnvZFofrnkpICSwDheHdEYlu0qwIekAGhH7n5rp8TbZn8_29cu_zwdfn5A7AyGSdxPyCbPWnK_cSoFpvXvk38xe_XDpg |
| linkToPdf | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9QwELaqIgEX3o_laaQeOODtxrGTmFuUslpeFVJbqZwi23Ek1JCtmixSOfHTmfE6oUCpKo5JnIk9Hmc-ZybfELI1S2Y1B1zNtDOSCV0rpiM7Y0LIysXCmMThp4GPu8niQLw7lIcbJBv-hYFOdCCp80F8XNXHVR0YBqLtcB4G1E8Tg8x0sO-5goE7tO282BvjB-CVlGdK5TFDfpiBb-h8IeiZbPe7Z_oLbp7rmbwXmt8kn8f---STo-mqN1P7_Q9qx_8Z4C1yI0BTmq9t6TbZcO0dcq0YKsLdJT8WpxU-uGEwqWgeFS30icHcdj-_dFnTvDlycNx_aekOGPc3zyvevaZnkpOobiua_wqc035JNZ0jeG7o3mkLkBSko7D9lXENFgT6ivF_mt8jB_M3-8WChQoOTMdp1jNuMiMqTCWNucq0SeH1AYDTZlZnKfjGyDqhFZLgibhSteSZ5M4Y4ZTRqal5fJ9stsvWPSQ0kUobqcDTgkOVqYVtGk-Uhv0pr4UVdkJegvbKsAK70gfXeVTiyaDSMqh0Qvgw0aUNTOhYkKO5-KZX403HayKQi5u_GCyohFnCKIxu3XIFHct8A8C9_27DsXRqOssEyHmwNr_xoRwLikmRTsjWWXscr3tKISWwHBSGeSckukyzIugBmRD6R5fX5XNy9dPOvPzwdvf9Y3Id0GSyzmV-Qjb7k5V7CoitN8_84vwJvMw84w |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Hydroxyl-Assisted+Carbonylation+of+Alkenyltin+Derivatives%3A+Development+and+Application+to+a+Formal+Synthesis+of+Tubelactomicin+A&rft.jtitle=Organic+letters&rft.au=Sommer%2C+Heiko&rft.au=Fuerstner%2C+Alois&rft.date=2016-07-01&rft.pub=Amer+Chemical+Soc&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=18&rft.issue=13&rft.spage=3210&rft.epage=3213&rft_id=info:doi/10.1021%2Facs.orglett.6b01431&rft_id=info%3Apmid%2F27280547&rft.externalDBID=n%2Fa&rft.externalDocID=000379455300043 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon |