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A concise asymmetric total synthesis of (+)-brevisamide.

ABSTRACT: A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A penultimate Stille cross-coupling allows for an efficient installation of the conjugated (E,E)-diene side chain ultimately delivering (+)-brevisamide.

SUBMITTER: Herrmann AT

PROVIDER: S-EPMC3365585 | biostudies-literature | 2011 Jul

REPOSITORIES: biostudies-literature

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A concise asymmetric total synthesis of (+)-brevisamide.

Herrmann Aaron T AT Martinez Steven R SR Zakarian Armen A

Organic letters 20110616 14

A new protecting-group-free synthesis of the marine monocyclic ether (+)-brevisamide is reported. The enantioselective synthesis utilizes a key asymmetric Henry reaction and an Achmatowicz rearrangement for the formation of the tetrahydropyran ring. A penultimate Stille cross-coupling allows for an efficient installation of the conjugated (E,E)-diene side chain ultimately delivering (+)-brevisamide. ...[more]

PMID: 21678904

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