Ring-closing metathesis approach to a 16-membered macrocycle of kendomycin
An approach to the macrocyclic core of kendomycin is described in which the Nozaki-Hiyama-Kishi coupling and a ring-closing olefin metathesis are the key reactions.
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Published in | Chemistry letters Vol. 36; no. 6; pp. 726 - 727 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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TOKYO
Chemical Soc Japan
05.06.2007
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Abstract | An approach to the macrocyclic core of kendomycin is described in which the Nozaki-Hiyama-Kishi coupling and a ring-closing olefin metathesis are the key reactions. |
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AbstractList | An approach to the macrocyclic core of kendomycin is described in which the Nozaki-Hiyama-Kishi coupling and a ring-closing olefin metathesis are the key reactions. |
Author | Uemura, Daisuke Arimoto, Hirokazu Sengoku, Tetsuya |
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Cites_doi | 10.1039/b602937j 10.1039/b402391a 10.1021/ol047779s 10.1021/ol0501875 10.1073/pnas.0401503101 10.1021/ja060369+ 10.1021/ol051512r 10.1021/jo010854h 10.1021/ja0447154 10.1016/S0040-4039(01)94157-7 10.1021/ol048825r 10.1039/b003362f 10.1021/ja051420x |
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Keywords | FRAGMENT (-)-KENDOMYCIN BIOSYNTHESIS STRATEGY |
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References | Bahnck, KB (WOS:000237951900025) 2006 (WOS:000247197800016.2) 1996 Green, MP (WOS:000223581900029) 2004; 6 Smith, AB (WOS:000236917200063) 2006; 128 Ghosh, AK (WOS:000172993000035) 2001; 66 Smith, AB (WOS:000229085200018) 2005; 127 Bode, HB (WOS:000085054900008) 2000 COREY EJ (WOS:000247197800016.6) 1972; 13 Williams, DR (WOS:000231858100025) 2005; 7 Martin, HJ (WOS:000170901400020) 2001; 40 Mulzer, J (WOS:000223410100014) 2004; 101 Lowe, JT (WOS:000228344200024) 2005; 7 Yuan, Y (WOS:000225083700020) 2004; 126 Sengoku, T (WOS:000222008300033) 2004 White, JD (WOS:000226330300018) 2005; 7 Bode, HB (WOS:000088767000017) 2000 (WOS:000247197800016.1) 1996 |
References_xml | – start-page: 2388 year: 2006 ident: WOS:000237951900025 article-title: Rapid stereocontrolled assembly of the fully substituted C-aryl glycoside of kendomycin with a Prins cyclization: a formal synthesis publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b602937j contributor: fullname: Bahnck, KB – start-page: 1220 year: 2004 ident: WOS:000222008300033 article-title: Synthetic approach to kendomycin: preparation of the C-glycosidic core publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b402391a contributor: fullname: Sengoku, T – year: 1996 ident: WOS:000247197800016.2 – volume: 7 start-page: 235 year: 2005 ident: WOS:000226330300018 article-title: Application of the Dotz reaction to construction of a major portion of the Ansa macrocycle (-)-kendomycin publication-title: ORGANIC LETTERS doi: 10.1021/ol047779s contributor: fullname: White, JD – volume: 7 start-page: 1529 year: 2005 ident: WOS:000228344200024 article-title: Stereocontrolled [4+2]-annulation accessing dihydropyrans: Synthesis of the C1a-C10 fragment of kendomycin publication-title: ORGANIC LETTERS doi: 10.1021/ol0501875 contributor: fullname: Lowe, JT – volume: 101 start-page: 11980 year: 2004 ident: WOS:000223410100014 article-title: Toward the synthesis of the carbacylic ansa antibiotic kendomycin publication-title: PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA doi: 10.1073/pnas.0401503101 contributor: fullname: Mulzer, J – volume: 128 start-page: 5292 year: 2006 ident: WOS:000236917200063 article-title: Evolution of a total synthesis of (-)-kendomycin exploiting a Petasis-Ferrier rearrangement/ring-closing olefin metathesis strategy publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja060369+ contributor: fullname: Smith, AB – volume: 7 start-page: 4161 year: 2005 ident: WOS:000231858100025 article-title: Efforts toward the total synthesis of (-)-kendomycin publication-title: ORGANIC LETTERS doi: 10.1021/ol051512r contributor: fullname: Williams, DR – volume: 66 start-page: 8973 year: 2001 ident: WOS:000172993000035 article-title: Total synthesis of microtubule-stabilizing agent (-)-laulimalide publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo010854h contributor: fullname: Ghosh, AK – volume: 126 start-page: 14720 year: 2004 ident: WOS:000225083700020 article-title: Total synthesis of kendomycin: A macro-C-glycosidation approach publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0447154 contributor: fullname: Yuan, Y – volume: 13 start-page: 3769 year: 1972 ident: WOS:000247197800016.6 publication-title: TETRAHEDRON LETT doi: 10.1016/S0040-4039(01)94157-7 contributor: fullname: COREY EJ – year: 1996 ident: WOS:000247197800016.1 – volume: 40 start-page: 3186 year: 2001 ident: WOS:000170901400020 article-title: Synthesis of the C1-C13 fragment of kendomycin: Atropisomerism around a C-aryl glycosidic bond publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Martin, HJ – volume: 6 start-page: 3131 year: 2004 ident: WOS:000223581900029 article-title: Synthesis of analogue structures of the p-quinone methide moiety of kendomycin publication-title: ORGANIC LETTERS doi: 10.1021/ol048825r contributor: fullname: Green, MP – start-page: 2665 year: 2000 ident: WOS:000088767000017 article-title: Biosynthesis of kendomycin: origin of the oxygen atoms and further investigations publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 doi: 10.1039/b003362f contributor: fullname: Bode, HB – volume: 127 start-page: 6948 year: 2005 ident: WOS:000229085200018 article-title: Total synthesis of (-)-kendomycin exploiting a petasis-ferrier rearrangement/ring-closing olefin metathesis synthetic strategy publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja051420x contributor: fullname: Smith, AB – start-page: 323 year: 2000 ident: WOS:000085054900008 article-title: Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: Bode, HB |
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Title | Ring-closing metathesis approach to a 16-membered macrocycle of kendomycin |
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