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Concise synthesis of (+)-fastigiatine.

ABSTRACT: (+)-Fastigiatine was assembled in six steps from (R)-5-methylcyclohex-2-en-1-one. Intermolecular Diels-Alder reaction introduced most of the carbon atoms for the target. The two Boc-protected nitrogen atom building blocks were introduced by a Suzuki coupling and a cuprate addition. A biomimetic transannular Mannich reaction generated the two quaternary centers at a late stage. Each step builds core bonds, and combined with a minimalist protecting group strategy, this approach led to a very concise synthesis.

SUBMITTER: Samame RA

PROVIDER: S-EPMC5580306 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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Concise synthesis of (+)-fastigiatine.

Samame Renzo A RA Owens Christina M CM Rychnovsky Scott D SD

Chemical science 20151006 1

(+)-Fastigiatine was assembled in six steps from (<i>R</i>)-5-methylcyclohex-2-en-1-one. Intermolecular Diels-Alder reaction introduced most of the carbon atoms for the target. The two Boc-protected nitrogen atom building blocks were introduced by a Suzuki coupling and a cuprate addition. A biomimetic transannular Mannich reaction generated the two quaternary centers at a late stage. Each step builds core bonds, and combined with a minimalist protecting group strategy, this approach led to a ver ...[more]

PMID: 28966768

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