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Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy.

ABSTRACT: A convergent synthetic route toward cytotoxic agent peloruside A that hinges on the use of an alkyne linchpin to assemble the natural product is described. Other highlights of this synthesis include an asymmetric desymmetrization reaction of a 1,3-diol, a one-pot conversion of a dibromoolefin to a stereodefined enone, and a diastereoselective aldol condensation. Misassignment of the absolute stereochemistry of the C18 stereocenter in our synthesis provided the natural product epimeric at the C18 ethyl stereocenter.

SUBMITTER: Trost BM

PROVIDER: S-EPMC3939827 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

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Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy.

Trost Barry M BM Michaelis David J DJ Malhotra Sushant S

Organic letters 20131004 20

A convergent synthetic route toward cytotoxic agent peloruside A that hinges on the use of an alkyne linchpin to assemble the natural product is described. Other highlights of this synthesis include an asymmetric desymmetrization reaction of a 1,3-diol, a one-pot conversion of a dibromoolefin to a stereodefined enone, and a diastereoselective aldol condensation. Misassignment of the absolute stereochemistry of the C18 stereocenter in our synthesis provided the natural product epimeric at the C18 ...[more]

PMID: 24490808

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