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Enantioselective syntheses of the proposed structures of cytotoxic macrolides iriomoteolide-1a and -1b.

ABSTRACT: Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that the reported structures have been assigned incorrectly. The synthesis features Julia-Kocienski olefination, Sharpless asymmetric epoxidation, Brown asymmetric crotylboration, a Sakurai reaction, an aldol reaction, and enzymatic resolution as the key steps.

SUBMITTER: Ghosh AK

PROVIDER: S-EPMC2920059 | biostudies-literature | 2010 Jul

REPOSITORIES: biostudies-literature

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Enantioselective syntheses of the proposed structures of cytotoxic macrolides iriomoteolide-1a and -1b.

Ghosh Arun K AK Yuan Hao H

Organic letters 20100701 14

Enantioselective total syntheses of the proposed structures of macrolide cytotoxic agents iriomoteolide-1a and -1b have been accomplished. The synthesis was carried out in a convergent and stereoselective manner. However, the present work suggests that the reported structures have been assigned incorrectly. The synthesis features Julia-Kocienski olefination, Sharpless asymmetric epoxidation, Brown asymmetric crotylboration, a Sakurai reaction, an aldol reaction, and enzymatic resolution as the k ...[more]

PMID: 20560539

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