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Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

ABSTRACT: A catalytic enantioselective formal total synthesis of aspergillide B is reported. This linchpin synthesis was enabled by the development of new conditions for Zn-ProPhenol catalyzed asymmetric alkyne addition. This reaction was used in conjunction with ruthenium-catalyzed trans-hydrosilylation to affect the rapid construction of a late-stage synthetic intermediate of aspergillide B to complete a formal synthesis of aspergillide B in a highly efficient manner.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3407809 | biostudies-literature | 2012 Mar

REPOSITORIES: biostudies-literature

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Transition-metal-catalyzed synthesis of aspergillide B: an alkyne addition strategy.

Trost Barry M BM Bartlett Mark J MJ

Organic letters 20120222 5

A catalytic enantioselective formal total synthesis of aspergillide B is reported. This linchpin synthesis was enabled by the development of new conditions for Zn-ProPhenol catalyzed asymmetric alkyne addition. This reaction was used in conjunction with ruthenium-catalyzed trans-hydrosilylation to affect the rapid construction of a late-stage synthetic intermediate of aspergillide B to complete a formal synthesis of aspergillide B in a highly efficient manner. ...[more]

PMID: 22356535

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