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Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.

ABSTRACT: A concise synthesis of (+/-)-pseudotabersonine from commercially available 1-(phenylsulfonyl)-3-indolecarboxaldehyde has been accomplished. This synthesis features the convergent assembly of a key intermediate via a stepwise variant of a Mannich-type multicomponent coupling process, a double ring-closing metathesis, and a one-pot deprotection/cyclization reaction.

SUBMITTER: Cheng B 

PROVIDER: S-EPMC2921645 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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Concise total synthesis of (+/-)-pseudotabersonine via double ring-closing metathesis strategy.

Cheng Bo B   Sunderhaus James D JD   Martin Stephen F SF  

Organic letters 20100801 16

A concise synthesis of (+/-)-pseudotabersonine from commercially available 1-(phenylsulfonyl)-3-indolecarboxaldehyde has been accomplished. This synthesis features the convergent assembly of a key intermediate via a stepwise variant of a Mannich-type multicomponent coupling process, a double ring-closing metathesis, and a one-pot deprotection/cyclization reaction. ...[more]

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