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Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

ABSTRACT: A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed.

SUBMITTER: Zhang H

PROVIDER: S-EPMC3910537 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Radical [3 + 2]-annulation of divinylcyclopropanes: rapid synthesis of complex meloscine analogs.

Zhang Hanmo H Jeon Kyu Ok KO Hay E Ben EB Geib Steven J SJ Curran Dennis P DP LaPorte Matthew G MG

Organic letters 20131206 1

A radical [3 + 2]-divinylcyclopropane annulation cascade has been extended to encompass five D-ring variants of the meloscine/epimeloscine core structure. Representative ABCD tetracyclic intermediates were further elaborated with novel substituted E-rings through subsequent transformations of advanced intermediates that provided opportunities for late-stage variation of the B-ring (lactam) N-substituents which were also developed. ...[more]

PMID: 24313360

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