Asymmetric Synthesis of (+)-Deoxoprosopinine
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| Published in | Journal of organic chemistry Vol. 66; no. 20; pp. 6829 - 6832 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
05.10.2001
Amer Chemical Soc |
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| Online Access | Get full text |
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| Author | Abad Grillo, Teresa Sandelier, Matthew J Comins, Daniel L |
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| Author_xml | – sequence: 1 givenname: Daniel L surname: Comins fullname: Comins, Daniel L – sequence: 2 givenname: Matthew J surname: Sandelier fullname: Sandelier, Matthew J – sequence: 3 givenname: Teresa surname: Abad Grillo fullname: Abad Grillo, Teresa |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/11578246$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1016_j_tetasy_2008_05_002 crossref_primary_10_1021_jo062365t crossref_primary_10_1021_ja020698b crossref_primary_10_1016_S0040_4039_03_00820_7 crossref_primary_10_1016_S0040_4039_03_00888_8 crossref_primary_10_1002_ejoc_200600777 crossref_primary_10_1016_j_tet_2006_08_014 crossref_primary_10_1002_chem_200901316 crossref_primary_10_1002_ejoc_200601040 crossref_primary_10_1081_SCC_120027272 crossref_primary_10_1002_ejoc_200800478 crossref_primary_10_1021_cr020101a crossref_primary_10_1016_j_tet_2006_09_072 crossref_primary_10_1016_S0957_4166_03_00123_X crossref_primary_10_1002_anie_200503467 crossref_primary_10_1016_j_tetasy_2007_08_028 crossref_primary_10_1002_ejoc_201801241 crossref_primary_10_1016_j_bmcl_2013_02_051 crossref_primary_10_1016_j_tet_2005_09_112 crossref_primary_10_1039_b804139c crossref_primary_10_1016_j_tetlet_2018_04_004 crossref_primary_10_1021_jo049108d crossref_primary_10_1016_S0040_4020_03_00295_3 crossref_primary_10_1039_b801671b crossref_primary_10_1016_j_tet_2015_12_057 crossref_primary_10_1002_ejoc_200500162 crossref_primary_10_1002_ejoc_201402603 crossref_primary_10_1002_ejoc_200901494 crossref_primary_10_1016_j_tetlet_2005_10_108 crossref_primary_10_1002_ejoc_201402363 crossref_primary_10_1021_jo049381f crossref_primary_10_1080_14328917_2004_11784822 crossref_primary_10_1039_C4RA14418J crossref_primary_10_1002_ange_200503467 crossref_primary_10_1021_jo100907u crossref_primary_10_1016_j_tetlet_2008_09_093 crossref_primary_10_1016_j_tetlet_2010_06_047 crossref_primary_10_1021_jo1019688 crossref_primary_10_1021_jo702350u crossref_primary_10_1002_chin_200212242 crossref_primary_10_1021_ol500498m |
| Cites_doi | 10.1021/ja00017a047 10.1021/ja00513a075 10.1039/C39930001838 10.1021/ol9908124 10.1016/S0040-4039(00)93628-1 10.1021/jo00026a004 10.1039/a807448h 10.1016/0040-4039(94)88315-7 10.1016/S0040-4039(00)75974-0 10.3987/COM-93-S125 10.1016/S0040-4039(98)01195-2 10.1002/bscb.19720810141 10.1021/jo9711495 10.1021/jo00071a005 10.1021/ja00090a019 10.1016/0040-4039(93)88003-2 10.1021/ja9626446 10.1021/jo990192k 10.1016/S0040-4039(98)02273-4 10.1021/ol990028j 10.1021/jo00196a002 10.1021/jo971448u 10.1021/jo00048a003 |
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| Copyright | Copyright © 2001 American Chemical Society |
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| DOI | 10.1021/jo015834u |
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| Keywords | ENANTIOPURE N-ACYLDIHYDROPYRIDONES PIPERIDINE ALKALOIDS (+)-DESOXOPROSOPININE RADICAL CYCLIZATION (-)-DEOXOPROSOPHYLLINE (-)-DESOXOPROSOPININE (+)-PROSOPININE INTRAMOLECULAR REACTION GAMMA-AMINOALLYLSTANNANE N-ACYL-2,3-DIHYDRO-4-PYRIDONES |
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| References | COMINS, DL (WOS:A1994NB47600055) 1994; 37 Comins, DL (WOS:000083701400017) 1999; 1 Ojima, I (WOS:000076781600062) 1998; 63 CIUFOLINI, MA (WOS:A1989U346600078) 1989; 111 Kadota, I (WOS:000071049800009) 1997; 8 SMITH, JG (WOS:A1984TR09700002) 1984; 49 COMINS, DL (WOS:A1994MV16900005) 1994; 35 Kuethe, JT (WOS:000085171900019) 1999; 1 TADANO, K (WOS:A1993LU13800009) 1993 COLVIN EW (WOS:000171407700049.4) 1988 Comins, DL (WOS:000074905500007) 1998; 39 YUASA, Y (WOS:A1995RR34900015) 1995; 6 Agami, C (WOS:000073490400041) 1998; 39 Kaufman, TS (WOS:000071627400015) 1997 Comins, DL (WOS:A1997YC65700065) 1997; 62 SAITOH, Y (WOS:A1981LF37800032) 1981; 54 TERAKADO, M (WOS:A1994NL31400011) 1994; 50 COOK, GR (WOS:A1994NA42700013) 1994; 35 Enders, D (WOS:000166020500017) 2000 Yuasa, Y (WOS:A1996UG78700010) 1996 Hirai, Y (WOS:A1997WJ67500002) 1997; 62 COMINS, DL (WOS:A1994NQ72300019) 1994; 116 SAITOH, Y (WOS:A1980HZ43600020) 1980; 21 Kadota, I (WOS:A1997YC43600046) 1997; 38 AYER WA (WOS:000171407700049.2) 1968; 11 HOLMES, AB (WOS:A1985TZ68800021) 1985 Yang, CF (WOS:000081957500004) 1999; 10 NATSUME, M (WOS:A1981LS13300021) 1981; 16 LUCHE, JL (WOS:A1979HL54400075) 1979; 101 KHUONGHUU, Q (WOS:A1972N192200006) 1972; 81 TAKAO, K (WOS:A1994NL31400010) 1994; 50 DESLONGCHAMPS P (WOS:000171407700049.12) 1983 Comins D. L. (jo015834ub00007/jo015834ub00007_5) 1994; 35 Luche J.-L. (jo015834ub00011/jo015834ub00011_1) 1979; 101 Colvin E. W. (jo015834ub00013/jo015834ub00013_1) 1988 Khuong-Huu Q. (jo015834ub00001/jo015834ub00001_1) 1972; 81 Comins D. L. (jo015834ub00008/jo015834ub00008_1) 1994; 116 Comins D. L. (jo015834ub00014/jo015834ub00014_1) 1994; 37 Comins D. L. (jo015834ub00005/jo015834ub00005_4) 1997; 62 Comins D. L. (jo015834ub00010/jo015834ub00010_1) 1998; 39 Previous (jo015834ub00004/jo015834ub00004_1) 1980; 21 Comins D. L. (jo015834ub00006/jo015834ub00006_4) 1992; 57 jo015834ub00009/jo015834ub00009_1 Comins D. L. (jo015834ub00005/jo015834ub00005_2) 1996; 118 jo015834ub00002/jo015834ub00002_1 Comins D. L. (jo015834ub00006/jo015834ub00006_3) 1993 Comins D. L. (jo015834ub00007/jo015834ub00007_3) 1993; 58 Comins D. L. (jo015834ub00011/jo015834ub00011_2) 1991; 56 Comins D. L. (jo015834ub00006/jo015834ub00006_2) 1999; 64 Kuethe J. T. (jo015834ub00012/jo015834ub00012_2) 1999; 1 Comins D. L. (jo015834ub00006/jo015834ub00006_1) 1999; 1 Previous (jo015834ub00003/jo015834ub00003_1) 1994; 35 Deslongchamps P. (jo015834ub00012/jo015834ub00012_1) 1983 Comins D. L. (jo015834ub00007/jo015834ub00007_2) 1998 Comins D. L. (jo015834ub00007/jo015834ub00007_1) 1998; 40 Comins D. L. (jo015834ub00005/jo015834ub00005_5) 1999 Al (jo015834ub00007/jo015834ub00007_4) 1992; 33 Comins D. L. (jo015834ub00005/jo015834ub00005_1) 1997; 62 Comins D. L. (jo015834ub00005/jo015834ub00005_3) 1991; 113 Smith J. G. (jo015834ub00013/jo015834ub00013_2) 1984; 49 |
| References_xml | – volume: 21 start-page: 75 year: 1980 ident: WOS:A1980HZ43600020 article-title: PIPERIDINE ALKALOIDS .5. CHIRAL AND STEREOSELECTIVE TOTAL SYNTHESIS OF (-)-DEOXOPROSOPININE AND (-)-DEOXOPROSOPHYLLINE publication-title: TETRAHEDRON LETTERS contributor: fullname: SAITOH, Y – volume: 39 start-page: 3505 year: 1998 ident: WOS:000073490400041 article-title: Total synthesis of (-)-desoxoprosopinine via the diastereoselective reduction of homochiral2-acyl-N-Boc-oxazolidines publication-title: TETRAHEDRON LETTERS contributor: fullname: Agami, C – volume: 35 start-page: 1669 year: 1994 ident: WOS:A1994NA42700013 article-title: AZA-ANNULATION AS A ROUTE TO HYDROXYLATED ALKALOID LIPIDS - THE SYNTHESIS OF (+/-)-PROSOPININE publication-title: TETRAHEDRON LETTERS contributor: fullname: COOK, GR – volume: 1 start-page: 229 year: 1999 ident: WOS:000083701400017 article-title: IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: Asymmetric synthesis of (+)-luciduline publication-title: ORGANIC LETTERS contributor: fullname: Comins, DL – volume: 1 start-page: 1031 year: 1999 ident: WOS:000085171900019 article-title: The Mukaiyama-Michael reaction of N-acyl-2,3-dihydro-4-pyridones: Regio- and stereoselective synthesis of cis-2,6-disubstituted 1,2,5,6-tetrahydropyridines publication-title: ORGANIC LETTERS contributor: fullname: Kuethe, JT – volume: 81 start-page: 425 year: 1972 ident: WOS:A1972N192200006 article-title: PIPERIDINE ALKALOIDS .2. STRUCTURE OF PROSOPINE AND PROSOPININE, ALKALOIDS FROM PROSOPIS-AFRICANA (GUILL AND PERR) TAUB publication-title: BULLETIN DES SOCIETES CHIMIQUES BELGES contributor: fullname: KHUONGHUU, Q – start-page: 37 year: 1985 ident: WOS:A1985TZ68800021 article-title: TOTAL SYNTHESIS OF (+/-)-ISOPROSOPININE-B AND (+/-)-DESOXOPROSOPININE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: HOLMES, AB – volume: 38 start-page: 7469 year: 1997 ident: WOS:A1997YC43600046 article-title: Total synthesis of (+)-desoxoprosopinine via the intramolecular reaction of gamma-aminoallylstannane publication-title: TETRAHEDRON LETTERS contributor: fullname: Kadota, I – volume: 37 start-page: 1121 year: 1994 ident: WOS:A1994NB47600055 article-title: REGIOSELECTIVE AND STEREOSELECTIVE ADDITION OF NUCLEOPHILES TO 1-PHENOXYCARBONYL-2,3-DIHYDROPYRIDINIUM SALTS publication-title: HETEROCYCLES contributor: fullname: COMINS, DL – volume: 62 start-page: 776 year: 1997 ident: WOS:A1997WJ67500002 article-title: Transition metal-mediated stereocontrolled cyclization of urethanes leading to versatile fused piperidines and its application to the synthesis of (+)-prosopinine and (+)-palustrine publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Hirai, Y – volume: 50 start-page: 5705 year: 1994 ident: WOS:A1994NL31400011 article-title: PALLADIUM(0)-CATALYZED CYCLIZATION-CARBONYLATION OF 2,7-OCTADIENYL ACETATE AND HOMOLOGS publication-title: TETRAHEDRON contributor: fullname: TERAKADO, M – volume: 63 start-page: 7999 year: 1998 ident: WOS:000076781600062 article-title: Rhodium-catalyzed cyclohydrocarbonylation: Application to the synthesis of (+)-prosopinine and (-)-deoxoprosophylline publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Ojima, I – volume: 111 start-page: 3473 year: 1989 ident: WOS:A1989U346600078 article-title: CHEMOENZYMATIC PREPARATION OF TRANS-2,6-DIALKYLPIPERIDINES AND OF OTHER AZACYCLE BUILDING-BLOCKS - TOTAL SYNTHESIS OF (+)-DESOXOPROSOPININE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: CIUFOLINI, MA – start-page: CH6 year: 1983 ident: WOS:000171407700049.12 publication-title: STEREOELECTRONIC EFF contributor: fullname: DESLONGCHAMPS P – volume: 62 start-page: 7435 year: 1997 ident: WOS:A1997YC65700065 article-title: Enantiopure N-acyldihydropyridones as synthetic intermediates: Asymmetric synthesis of (-)-septicine and (-)-tylophorine publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Comins, DL – volume: 54 start-page: 488 year: 1981 ident: WOS:A1981LF37800032 article-title: PIPERIDINE ALKALOIDS (ALCALOIDES PIPERIDINIQUES) .6. CHIRAL AND STEREOSELECTIVE TOTAL SYNTHESIS OF (-)-DEOXOPROSOPININE AND (-)-DEOXOPROSOPHYLLINE - INTRAMOLECULAR AMINOMERCURATION OF AN EPSILON,ZETA-UNSATURATED AMINE publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN contributor: fullname: SAITOH, Y – volume: 50 start-page: 5681 year: 1994 ident: WOS:A1994NL31400010 article-title: STEREOSELECTIVE TOTAL SYNTHESES OF (-)-DESOXOPROSOPININE AND (-)-DESOXOPROSOPHYLLINE - PALLADIUM(0)-CATALYZED INTRAMOLECULAR N-ALKYLATION FOR THE KEY PIPERIDINE RING FORMATION publication-title: TETRAHEDRON contributor: fullname: TAKAO, K – volume: 49 start-page: 4112 year: 1984 ident: WOS:A1984TR09700002 article-title: REGIOSELECTIVE SYNTHESIS OF ALLYLTRIMETHYLSILANES FROM ALLYLIC HALIDES AND ALLYLIC SULFONATES - APPLICATION TO THE SYNTHESIS OF 2,3-BIS(TRIMETHYLSILYL)ALK-1-ENES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SMITH, JG – volume: 39 start-page: 5693 year: 1998 ident: WOS:000074905500007 article-title: C-3 acetoxylation of N-acyl-2,3-dihydro-4-pyridones publication-title: TETRAHEDRON LETTERS contributor: fullname: Comins, DL – volume: 16 start-page: 973 year: 1981 ident: WOS:A1981LS13300021 article-title: TOTAL SYNTHESIS OF PROSOPHYLLINE publication-title: HETEROCYCLES contributor: fullname: NATSUME, M – volume: 10 start-page: 2311 year: 1999 ident: WOS:000081957500004 article-title: New concise asymmetric total synthesis of (+)-desoxoprosophylline and prosophylline publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: Yang, CF – volume: 116 start-page: 4719 year: 1994 ident: WOS:A1994NQ72300019 article-title: ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: COMINS, DL – volume: 11 start-page: 492 year: 1968 ident: WOS:000171407700049.2 publication-title: ALKALOIDS contributor: fullname: AYER WA – start-page: 565 year: 1993 ident: WOS:A1993LU13800009 article-title: STEREOSELECTIVE TOTAL SYNTHESES OF (-)-DESOXOPROSOPININE AND (-)-DESOXOPROSOPHYLLINE - PALLADIUM(0)-CATALYZED INTRAMOLECULAR N-ALKYLATION FOR THE KEY PIPERIDINE RING FORMATION publication-title: SYNLETT contributor: fullname: TADANO, K – start-page: CH5 year: 1988 ident: WOS:000171407700049.4 publication-title: SILICON REAGENTS ORG contributor: fullname: COLVIN EW – volume: 35 start-page: 829 year: 1994 ident: WOS:A1994MV16900005 article-title: ENANTIOPURE N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - AN ASYMMETRIC-SYNTHESIS OF SOLENOPSIN-A publication-title: TETRAHEDRON LETTERS contributor: fullname: COMINS, DL – start-page: 793 year: 1996 ident: WOS:A1996UG78700010 article-title: Diastereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidine and 2,6-disubstituted 3-hydroxypiperidine derivatives by radical cyclisation; Synthesis of (+)-bulgecinine and (-)-desoxoprosopinine publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: Yuasa, Y – volume: 6 start-page: 1525 year: 1995 ident: WOS:A1995RR34900015 article-title: ENANTIOSELECTIVE SYNTHESIS OF (-)-DESOXOPROSOPININE BY RADICAL CYCLIZATION publication-title: TETRAHEDRON-ASYMMETRY contributor: fullname: YUASA, Y – start-page: 1377 year: 1997 ident: WOS:000071627400015 article-title: Convenient one-pot synthesis of primary alpha-alkoxystannanes publication-title: SYNLETT contributor: fullname: Kaufman, TS – volume: 101 start-page: 5848 year: 1979 ident: WOS:A1979HL54400075 article-title: LANTHANOIDS IN ORGANIC-SYNTHESIS .5. 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| SubjectTerms | Alkaloids - chemical synthesis Analgesics - chemical synthesis Anesthetics - chemical synthesis Anti-Bacterial Agents - chemical synthesis Chemistry Chemistry, Organic Oxidation-Reduction Physical Sciences Piperidines - chemical synthesis Plants, Medicinal - chemistry Science & Technology Stereoisomerism |
| Title | Asymmetric Synthesis of (+)-Deoxoprosopinine |
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