Total Synthesis of Gymnocin‑A
A convergent total synthesis of cytotoxic marine natural polycyclic ether, gymnocin-A (1), is described. The synthesis features three iterations of an oxiranyl anion strategy, involving base-mediated cycloetherification, ring expansion, and reductive etherification, for the construction of the FGH f...
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| Published in | Journal of the American Chemical Society Vol. 137; no. 45; pp. 14513 - 14516 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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18.11.2015
Amer Chemical Soc |
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| Abstract | A convergent total synthesis of cytotoxic marine natural polycyclic ether, gymnocin-A (1), is described. The synthesis features three iterations of an oxiranyl anion strategy, involving base-mediated cycloetherification, ring expansion, and reductive etherification, for the construction of the FGH fragment and for its coupling with the ABC and KLMN fragments. |
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| AbstractList | A convergent total synthesis of cytotoxic marine natural polycyclic ether, gymnocin-A (1), is described. The synthesis features three iterations of an oxiranyl anion strategy, involving base-mediated cycloetherification, ring expansion, and reductive etherification, for the construction of the FGH fragment and for its coupling with the ABC and KLMN fragments. |
| Author | Mori, Yuji Matsushita, Shingo Yoshida, Tatsuji Sakai, Takeo Arakawa, Shogo Tanimoto, Miki Mori, Koichi Tokumasu, Akihiro |
| AuthorAffiliation | Meijo University Faculty of Pharmacy |
| AuthorAffiliation_xml | – name: Meijo University – name: Faculty of Pharmacy |
| Author_xml | – sequence: 1 givenname: Takeo surname: Sakai fullname: Sakai, Takeo – sequence: 2 givenname: Shingo surname: Matsushita fullname: Matsushita, Shingo – sequence: 3 givenname: Shogo surname: Arakawa fullname: Arakawa, Shogo – sequence: 4 givenname: Koichi surname: Mori fullname: Mori, Koichi – sequence: 5 givenname: Miki surname: Tanimoto fullname: Tanimoto, Miki – sequence: 6 givenname: Akihiro surname: Tokumasu fullname: Tokumasu, Akihiro – sequence: 7 givenname: Tatsuji surname: Yoshida fullname: Yoshida, Tatsuji – sequence: 8 givenname: Yuji surname: Mori fullname: Mori, Yuji email: mori@meijo-u.ac.jp |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26521846$$D View this record in MEDLINE/PubMed |
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| CitedBy_id | crossref_primary_10_1039_D1OB01905H crossref_primary_10_5059_yukigoseikyokaishi_74_965 crossref_primary_10_5059_yukigoseikyokaishi_79_874 crossref_primary_10_1248_yakushi_17_00116 crossref_primary_10_1016_j_tetlet_2019_151515 crossref_primary_10_5059_yukigoseikyokaishi_77_424 crossref_primary_10_3987_COM_17_S_T_8 crossref_primary_10_1021_acs_joc_7b00232 crossref_primary_10_5059_yukigoseikyokaishi_82_733 crossref_primary_10_1021_acs_joc_6b00484 crossref_primary_10_1002_hlca_201900161 crossref_primary_10_1038_s41570_018_0115 crossref_primary_10_1002_chem_202400234 crossref_primary_10_1021_acs_joc_2c02414 crossref_primary_10_1039_D4QO00380B crossref_primary_10_3390_molecules28217303 crossref_primary_10_1002_chem_201704776 crossref_primary_10_1021_acs_orglett_9b02502 crossref_primary_10_1248_cpb_c18_00699 crossref_primary_10_1016_j_tetlet_2019_151261 crossref_primary_10_3390_ijms24076195 |
| Cites_doi | 10.1021/ja038547b 10.1039/b705664h 10.1039/b919467n 10.1021/ja212116q 10.1021/ol102925d 10.1021/ol202467z 10.1002/chem.201201346 10.1021/ol302032w 10.1016/j.tetlet.2005.03.115 10.1021/ol500788c 10.1021/cr0406108 10.1021/ol9017408 10.1021/ja0512677 10.1021/np100729d 10.1016/j.tetlet.2014.10.014 10.3987/COM-12-12814 10.1021/ja0279646 10.1021/ol800685c 10.1021/ol802710u 10.1002/anie.200900924 10.1002/anie.200801696 10.1002/chem.201204303 10.1021/jo302267f 10.1021/cr040627q 10.1021/ol900769d 10.1021/jo502426p 10.1021/ja200089f 10.1021/ja305864z 10.1016/j.tetlet.2006.07.081 10.1002/tcr.1010 10.1039/a908456h 10.1016/S0040-4039(02)01171-1 10.1016/S0040-4039(00)74101-3 10.1248/cpb.30.119 10.1080/00397919708003328 10.1039/a901979k 10.1016/0040-4039(80)80089-X 10.1016/S0040-4020(97)00816-8 10.1016/S0040-4039(01)80205-7 10.1016/S0041-0101(00)00255-5 10.1016/S0040-4039(01)93909-7 10.1021/cr00021a002 10.1021/cr00021a011 10.1021/ja042686r |
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| Keywords | ORGANIC-SYNTHESIS RING EXPANSION GYMNODINIUM-MIKIMOTOI POLYETHER FUSED POLYCYCLIC ETHERS RED TIDE DINOFLAGELLATE STEREOSELECTIVE-SYNTHESIS BETA-ALKOXYACRYLATES MARINE TOXINS CONVERGENT STRATEGIES |
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| References | Daranas, AH (WOS:000168881200001) 2001; 39 Van Dyke, AR (WOS:000267040000035) 2009; 48 Nicolaou, KC (WOS:000259382900011) 2008; 47 Doi, R (WOS:000347506400040) 2015; 80 Sakai, T (WOS:000345488900011) 2014; 55 Fuwa, H (WOS:000306724500041) 2012; 134 Kornprobst, J.-M (000365148500039.15) 2010; 1 Satake, M (000365148500039.32) 2006; 5 Kuranaga, T (WOS:000287122800039) 2011; 13 Crimmins, MT (WOS:000262293500059) 2009; 11 LEE, E (WOS:A1993LN88200028) 1993; 34 Liu, HQ (WOS:000308579100007) 2012; 18 Sasaki, M (WOS:000254647800009) 2008; 25 Hamamoto, Y (WOS:000301990600073) 2012; 134 Furuta, H (WOS:000269989100034) 2009; 11 Tsukano, C (WOS:000186722200042) 2003; 125 Tanaka, Y (WOS:000326771700005) 2013; 87 Tsukano, C (WOS:000240670800022) 2006; 47 Sakai, T (WOS:000312564900019) 2012; 77 Tanaka, K (WOS:000230220900058) 2005; 127 Ebine, M (WOS:000256281600047) 2008; 10 HASHIMOTO, N (WOS:A1980KS00200014) 1980; 21 YASUMOTO, T (WOS:A1993LU76000012) 1993; 93 Zhang, YA (WOS:000289455200061) 2011; 133 Jeong, EJ (WOS:000179661000037) 2002; 124 Satake, M (WOS:000177263600031) 2002; 43 HASHIMOTO, N (WOS:A1982NC71100016) 1982; 30 BLANCHETTE, MA (WOS:A1984SR17900002) 1984; 25 Sakai, T (WOS:000334823600050) 2014; 16 Lee, E. (000365148500039.18) 1999; 1 Tsukano, C (WOS:000227895500052) 2005; 127 TOSHIMA, K (WOS:A1989CB56400044) 1989; 30 Murata, M (WOS:000087151900006) 2000; 17 Satake, M (WOS:000228872300023) 2005; 46 Isobe, M (WOS:000280147000007) 2010; 27 Yamashita, S (WOS:000288691800009) 2011; 74 Yuasa, Y (WOS:A1997WJ30200006) 1997; 27 Sakai, T (WOS:000296212200037) 2011; 13 Inoue, M (WOS:000234118000005) 2005; 105 Ishigai, K (WOS:000317894300010) 2013; 19 SHIMIZU, Y (WOS:A1993LU76000003) 1993; 93 Takamura, H (WOS:000266930900014) 2009; 11 Shimizu, Y (000365148500039.33) 1978; 1 Mori, Y (WOS:A1997XW84000009) 1997; 53 Nakata, T (WOS:000234118000003) 2005; 105 Sakai, T (WOS:000308390000069) 2012; 14 Yasumoto, T (WOS:000182372000004) 2001; 1 ref9/cit9 ref1/cit1h ref3/cit3 ref1/cit1e ref1/cit1d ref1/cit1g ref1/cit1f ref11/cit11 ref8/cit8a ref12/cit12e ref8/cit8b ref12/cit12d ref12/cit12c ref12/cit12b ref12/cit12a ref2/cit2b ref2/cit2a ref1/cit1a ref1/cit1c ref5/cit5b ref5/cit5c ref10/cit10 Shimizu Y. (ref1/cit1b) 1978; 1 ref5/cit5a ref4/cit4a ref4/cit4b ref14/cit14a ref14/cit14c ref14/cit14b ref15/cit15 ref14/cit14d ref13/cit13 ref5/cit5n ref5/cit5l ref5/cit5m ref5/cit5j ref5/cit5k ref6/cit6a ref5/cit5h ref6/cit6b ref5/cit5i ref6/cit6c ref5/cit5f ref5/cit5g ref5/cit5d ref5/cit5e ref7/cit7 |
| References_xml | – volume: 125 start-page: 14294 year: 2003 ident: WOS:000186722200042 article-title: Total synthesis of gymnocin-A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja038547b contributor: fullname: Tsukano, C – volume: 25 start-page: 401 year: 2008 ident: WOS:000254647800009 article-title: Convergent strategies for the total synthesis of polycyclic ether marine metabolites publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/b705664h contributor: fullname: Sasaki, M – volume: 27 start-page: 1204 year: 2010 ident: WOS:000280147000007 article-title: Ciguatoxin: developing the methodology for total synthesis publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/b919467n contributor: fullname: Isobe, M – volume: 17 start-page: 293 year: 2000 ident: WOS:000087151900006 article-title: The structure elucidation and biological activities of high molecular weight algal toxins: maitotoxin, prymnesins and zooxanthellatoxins publication-title: NATURAL PRODUCT REPORTS contributor: fullname: Murata, M – volume: 134 start-page: 4963 year: 2012 ident: WOS:000301990600073 article-title: Brevisulcenal-F: A Polycyclic Ether Toxin Associated with Massive Fish-kills in New Zealand publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja212116q contributor: fullname: Hamamoto, Y – volume: 30 start-page: 6413 year: 1989 ident: WOS:A1989CB56400044 article-title: THE DIETHYLISOPROPYLSILYL GROUP - A NEW PROTECTING GROUP FOR ALCOHOLS publication-title: TETRAHEDRON LETTERS contributor: fullname: TOSHIMA, K – volume: 1 start-page: 3395 year: 1999 ident: 000365148500039.18 publication-title: J. Chem. Soc., Perkin Trans. 1 contributor: fullname: Lee, E. – volume: 13 start-page: 696 year: 2011 ident: WOS:000287122800039 article-title: Total Synthesis of (-)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether publication-title: ORGANIC LETTERS doi: 10.1021/ol102925d contributor: fullname: Kuranaga, T – volume: 13 start-page: 5850 year: 2011 ident: WOS:000296212200037 article-title: A Convergent Strategy for the Synthesis of Polycyclic Ethers by Using Oxiranyl Anions publication-title: ORGANIC LETTERS doi: 10.1021/ol202467z contributor: fullname: Sakai, T – volume: 18 start-page: 11889 year: 2012 ident: WOS:000308579100007 article-title: New Methylene Homologation Method for Cyclic Ketones publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201201346 contributor: fullname: Liu, HQ – volume: 14 start-page: 4564 year: 2012 ident: WOS:000308390000069 article-title: Mechanism of the Regio- and Diastereoselective Ring Expansion Reaction Using Trimethylsilyldiazomethane publication-title: ORGANIC LETTERS doi: 10.1021/ol302032w contributor: fullname: Sakai, T – volume: 27 start-page: 573 year: 1997 ident: WOS:A1997WJ30200006 article-title: Diastereoselective synthesis of cyclic ethers by radical cyclization at beta-position of beta-alkoxyacrylates publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: Yuasa, Y – volume: 30 start-page: 119 year: 1982 ident: WOS:A1982NC71100016 article-title: NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .18. HOMOLOGATION OF KETONES WITH TRIMETHYLSILYLDIAZOMETHANE (TMSCHN2) publication-title: CHEMICAL & PHARMACEUTICAL BULLETIN contributor: fullname: HASHIMOTO, N – volume: 46 start-page: 3537 year: 2005 ident: WOS:000228872300023 article-title: Gymnocin-B with the largest contiguous polyether rings from the red tide dinotlagellate, Karenia (formerly Gymnodinium) mikimotoi publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2005.03.115 contributor: fullname: Satake, M – volume: 93 start-page: 1897 year: 1993 ident: WOS:A1993LU76000012 article-title: MARINE TOXINS publication-title: CHEMICAL REVIEWS contributor: fullname: YASUMOTO, T – volume: 43 start-page: 5829 year: 2002 ident: WOS:000177263600031 article-title: Gymnocin-A, a cytotoxic polyether from the notorious red tide dinoflagellate, Gymnodinium mikimotoi publication-title: TETRAHEDRON LETTERS contributor: fullname: Satake, M – volume: 21 start-page: 4619 year: 1980 ident: WOS:A1980KS00200014 article-title: NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .10. "TRIMETHYLSILYLDIAZOMETHANE(TMSCHN2) - A NEW, STABLE, AND SAFE REAGENT FOR THE HOMOLOGATION OF KETONES publication-title: TETRAHEDRON LETTERS contributor: fullname: HASHIMOTO, N – volume: 16 start-page: 2268 year: 2014 ident: WOS:000334823600050 article-title: Synthesis of the KLMN Fragment of Gymnocin-A Using Oxiranyl Anion Convergent Methodology publication-title: ORGANIC LETTERS doi: 10.1021/ol500788c contributor: fullname: Sakai, T – volume: 105 start-page: 4379 year: 2005 ident: WOS:000234118000005 article-title: Convergent strategies for syntheses of trans-fused polycyclic ethers publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0406108 contributor: fullname: Inoue, M – volume: 11 start-page: 4382 year: 2009 ident: WOS:000269989100034 article-title: Total Synthesis of Gambierol publication-title: ORGANIC LETTERS doi: 10.1021/ol9017408 contributor: fullname: Furuta, H – volume: 127 start-page: 9561 year: 2005 ident: WOS:000230220900058 article-title: Three challenges toward the assignment of absolute configuration of gymnocin-B publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0512677 contributor: fullname: Tanaka, K – volume: 74 start-page: 357 year: 2011 ident: WOS:000288691800009 article-title: Stereoselective 6-exo Radical Cyclization Using cis-Vinyl Sulfoxide: Practical Total Synthesis of CTX3C publication-title: JOURNAL OF NATURAL PRODUCTS doi: 10.1021/np100729d contributor: fullname: Yamashita, S – volume: 5 start-page: 21 year: 2006 ident: 000365148500039.32 publication-title: Topics in Heterocyclic Chemistry contributor: fullname: Satake, M – volume: 25 start-page: 2183 year: 1984 ident: WOS:A1984SR17900002 article-title: HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS publication-title: TETRAHEDRON LETTERS contributor: fullname: BLANCHETTE, MA – volume: 39 start-page: 1101 year: 2001 ident: WOS:000168881200001 article-title: Toxic marine microalgae publication-title: TOXICON contributor: fullname: Daranas, AH – volume: 1 start-page: 212 year: 2010 ident: 000365148500039.15 publication-title: Encyclopedia of Marine Natural Products contributor: fullname: Kornprobst, J.-M – volume: 53 start-page: 12917 year: 1997 ident: WOS:A1997XW84000009 article-title: Stereoselective synthesis of the 6,7,6- and 6,7,7-ring systems of polycyclic ethers by 6-endo cyclization and ring expansion publication-title: TETRAHEDRON contributor: fullname: Mori, Y – volume: 55 start-page: 6557 year: 2014 ident: WOS:000345488900011 article-title: Synthetic study of gymnocin-A: synthesis of the ABC ring fragment publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2014.10.014 contributor: fullname: Sakai, T – volume: 93 start-page: 1685 year: 1993 ident: WOS:A1993LU76000003 article-title: MICROALGAL METABOLITES publication-title: CHEMICAL REVIEWS contributor: fullname: SHIMIZU, Y – volume: 1 start-page: 228 year: 2001 ident: WOS:000182372000004 article-title: The chemistry and biological function of natural marine toxins publication-title: CHEMICAL RECORD contributor: fullname: Yasumoto, T – volume: 87 start-page: 2037 year: 2013 ident: WOS:000326771700005 article-title: GYMNOCIN-A CARBOXYLIC ACID AND GYMNOCIN-A2, CYTOTOXIC POLYETHERS FROM THE RED TIDE DINOFLAGELLATE KARENIA MIKIMOTOI publication-title: HETEROCYCLES doi: 10.3987/COM-12-12814 contributor: fullname: Tanaka, Y – volume: 124 start-page: 14655 year: 2002 ident: WOS:000179661000037 article-title: Stereoselective synthesis of pamamycin-607 publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0279646 contributor: fullname: Jeong, EJ – volume: 10 start-page: 2275 year: 2008 ident: WOS:000256281600047 article-title: Total synthesis of (-)-brevenal: A concise synthetic entry to the pentacyclic polyether core publication-title: ORGANIC LETTERS doi: 10.1021/ol800685c contributor: fullname: Ebine, M – volume: 11 start-page: 489 year: 2009 ident: WOS:000262293500059 article-title: Total Synthesis of Brevetoxin A publication-title: ORGANIC LETTERS doi: 10.1021/ol802710u contributor: fullname: Crimmins, MT – volume: 48 start-page: 4430 year: 2009 ident: WOS:000267040000035 article-title: Functionalized Templates for the Convergent Assembly of Polyethers: Synthesis of the HIJK Rings of Gymnocin A publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200900924 contributor: fullname: Van Dyke, AR – volume: 47 start-page: 7182 year: 2008 ident: WOS:000259382900011 article-title: The continuing saga of the marine polyether biotoxins publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200801696 contributor: fullname: Nicolaou, KC – volume: 19 start-page: 5276 year: 2013 ident: WOS:000317894300010 article-title: Total Synthesis and Biological Evaluation of (+)-Gambieric Acid A and Its Analogues publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201204303 contributor: fullname: Ishigai, K – volume: 77 start-page: 11177 year: 2012 ident: WOS:000312564900019 article-title: Divergent Synthesis of Trans-Fused Polycyclic Ethers by a Convergent Oxiranyl Anion Strategy publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo302267f contributor: fullname: Sakai, T – volume: 1 year: 1978 ident: 000365148500039.33 article-title: Dinoflagellate Toxins publication-title: Marine Natural Products contributor: fullname: Shimizu, Y – volume: 105 start-page: 4314 year: 2005 ident: WOS:000234118000003 article-title: Total syntheses of marine polycyclic ethers publication-title: CHEMICAL REVIEWS doi: 10.1021/cr040627q contributor: fullname: Nakata, T – volume: 11 start-page: 2531 year: 2009 ident: WOS:000266930900014 article-title: Total Synthesis of Brevenal publication-title: ORGANIC LETTERS doi: 10.1021/ol900769d contributor: fullname: Takamura, H – volume: 34 start-page: 4831 year: 1993 ident: WOS:A1993LN88200028 article-title: BETA-ALKOXYACRYLATES IN RADICAL CYCLIZATIONS - REMARKABLY EFFICIENT OXACYCLE SYNTHESIS publication-title: TETRAHEDRON LETTERS contributor: fullname: LEE, E – volume: 127 start-page: 4326 year: 2005 ident: WOS:000227895500052 article-title: Convergent total synthesis of gymnocin-A and evaluation of synthetic analogues publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Tsukano, C – volume: 80 start-page: 401 year: 2015 ident: WOS:000347506400040 article-title: Development of an Azanoradamantane-Type Nitroxyl Radical Catalyst for Class-Selective Oxidation of Alcohols publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo502426p contributor: fullname: Doi, R – volume: 133 start-page: 3208 year: 2011 ident: WOS:000289455200061 article-title: Total Synthesis of Brevenal publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja200089f contributor: fullname: Zhang, YA – volume: 134 start-page: 11984 year: 2012 ident: WOS:000306724500041 article-title: Total Synthesis and Complete Stereostructure of Gambieric Acid A publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja305864z contributor: fullname: Fuwa, H – volume: 47 start-page: 6803 year: 2006 ident: WOS:000240670800022 article-title: Structure-activity relationship studies of gymnocin-A publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2006.07.081 contributor: fullname: Tsukano, C – ident: ref1/cit1f doi: 10.1002/tcr.1010 – ident: ref10/cit10 doi: 10.1021/ol500788c – ident: ref14/cit14c doi: 10.1039/a908456h – ident: ref5/cit5m doi: 10.1021/ja305864z – ident: ref5/cit5e doi: 10.1039/b919467n – ident: ref15/cit15 doi: 10.1021/jo502426p – ident: ref5/cit5b doi: 10.1021/cr040627q – ident: ref5/cit5k doi: 10.1021/np100729d – ident: ref2/cit2a doi: 10.1016/S0040-4039(02)01171-1 – ident: ref7/cit7 doi: 10.1002/anie.200900924 – ident: ref14/cit14a doi: 10.1016/S0040-4039(00)74101-3 – ident: ref6/cit6a doi: 10.1021/ja038547b – ident: ref5/cit5n doi: 10.1002/chem.201204303 – ident: ref5/cit5f doi: 10.1021/ol800685c – ident: ref5/cit5i doi: 10.1021/ol9017408 – ident: ref12/cit12b doi: 10.1248/cpb.30.119 – ident: ref14/cit14b doi: 10.1080/00397919708003328 – ident: ref9/cit9 doi: 10.1016/j.tetlet.2014.10.014 – ident: ref14/cit14d doi: 10.1021/ja0279646 – ident: ref1/cit1e doi: 10.1039/a901979k – ident: ref5/cit5g doi: 10.1021/ol802710u – ident: ref8/cit8b doi: 10.1021/jo302267f – ident: ref1/cit1a – ident: ref12/cit12e doi: 10.1002/chem.201201346 – ident: ref5/cit5c doi: 10.1002/anie.200801696 – ident: ref12/cit12a doi: 10.1016/0040-4039(80)80089-X – ident: ref12/cit12c doi: 10.1016/S0040-4020(97)00816-8 – ident: ref8/cit8a doi: 10.1021/ol202467z – ident: ref13/cit13 doi: 10.1016/S0040-4039(01)80205-7 – ident: ref3/cit3 doi: 10.1021/ja212116q – ident: ref1/cit1g doi: 10.1016/S0041-0101(00)00255-5 – ident: ref5/cit5j doi: 10.1021/ja200089f – ident: ref4/cit4b doi: 10.1021/ja0512677 – ident: ref5/cit5d doi: 10.1039/b705664h – ident: ref2/cit2b doi: 10.3987/COM-12-12814 – ident: ref12/cit12d doi: 10.1021/ol302032w – volume: 1 volume-title: Marine Natural Products year: 1978 ident: ref1/cit1b contributor: fullname: Shimizu Y. – ident: ref5/cit5h doi: 10.1021/ol900769d – ident: ref5/cit5l doi: 10.1021/ol102925d – ident: ref11/cit11 doi: 10.1016/S0040-4039(01)93909-7 – ident: ref1/cit1c doi: 10.1021/cr00021a002 – ident: ref1/cit1h – ident: ref5/cit5a doi: 10.1021/cr0406108 – ident: ref1/cit1d doi: 10.1021/cr00021a011 – ident: ref6/cit6b doi: 10.1021/ja042686r – ident: ref4/cit4a doi: 10.1016/j.tetlet.2005.03.115 – ident: ref6/cit6c doi: 10.1016/j.tetlet.2006.07.081 |
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| Snippet | A convergent total synthesis of cytotoxic marine natural polycyclic ether, gymnocin-A (1), is described. The synthesis features three iterations of an oxiranyl... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Ethers, Cyclic - chemical synthesis Ethers, Cyclic - chemistry Molecular Conformation Physical Sciences Science & Technology Stereoisomerism |
| Title | Total Synthesis of Gymnocin‑A |
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