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Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

ABSTRACT: A concise, nine-step enantioselective total synthesis of metacycloprodigiosin is reported. The synthesis provides increased step-efficiency over the previous racemic and enantioselective syntheses of this compound. Key features of the work include investigations into a convergent oxidative coupling reaction and subsequent ring-closing metathesis to deliver an advanced pyrrole intermediate we name the "Wasserman pyrrole" that can be converted to metacycloprodigiosin in one step.

SUBMITTER: Vega MM

PROVIDER: S-EPMC4480779 | biostudies-literature | 2015 Jun

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of metacycloprodigiosin via the "Wasserman pyrrole".

Vega Marvin M MM Crain Diana M DM Konkol Leah C LC Thomson Regan J RJ

Tetrahedron letters 20150601 23

A concise, nine-step enantioselective total synthesis of metacycloprodigiosin is reported. The synthesis provides increased step-efficiency over the previous racemic and enantioselective syntheses of this compound. Key features of the work include investigations into a convergent oxidative coupling reaction and subsequent ring-closing metathesis to deliver an advanced pyrrole intermediate we name the "Wasserman pyrrole" that can be converted to metacycloprodigiosin in one step. ...[more]

PMID: 26120213

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