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Search for highly efficient, stereoselective, and practical synthesis of complex organic compounds of medicinal importance as exemplified by the synthesis of the C21-C37 fragment of amphotericin?B.

ABSTRACT: Highly stereoselective: A highly efficient, stereoselective and practical synthesis of the C21-C37 fragment of amphotericin?B was realized in 25?% overall yield in eight longest linear steps from commercially available ethyl (S)-3-hydroxybutyrate by using Fráter-Seebach alkylation, Brown crotylboration, Negishi coupling, Heck reaction, and Horner-Wadsworth-Emmons (HWE) olefination as key steps (see diagram).

SUBMITTER: Wang G

PROVIDER: S-EPMC3846173 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Search for highly efficient, stereoselective, and practical synthesis of complex organic compounds of medicinal importance as exemplified by the synthesis of the C21-C37 fragment of amphotericin B.

Wang Guangwei G Xu Shiqing S Hu Qian Q Zeng Fanxing F Negishi Ei-ichi E

Chemistry (Weinheim an der Bergstrasse, Germany) 20130903 39

Highly stereoselective: A highly efficient, stereoselective and practical synthesis of the C21-C37 fragment of amphotericin B was realized in 25 % overall yield in eight longest linear steps from commercially available ethyl (S)-3-hydroxybutyrate by using Fráter-Seebach alkylation, Brown crotylboration, Negishi coupling, Heck reaction, and Horner-Wadsworth-Emmons (HWE) olefination as key steps (see diagram). ...[more]

PMID: 24038187

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