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Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.

ABSTRACT: A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed.

SUBMITTER: Ghosh P

PROVIDER: S-EPMC3044927 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

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Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.

Ghosh Partha P Zhang Yue Y Emge Thomas J TJ Williams Lawrence J LJ

Organic letters 20091001 19

A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed. ...[more]

PMID: 19725523

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