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Total synthesis of (+)-18-epi-latrunculol A: development of a synthetic route.

ABSTRACT: The evolution of an enantioselective total synthesis of (+)-18-epi-latrunculol A, a congener of the marine-sponge-derived latrunculins A and B, is reported. Key steps include a late-stage Mitsunobu macrolactonization to construct the 16-membered macrolactone, a mild Carreira alkynylation to unite the northern and southern hemispheres, a diastereoselective, acid-mediated ?-hydroxy enone cyclization/equilibration sequence, and a functional-group-tolerant cross-metathesis to access the enone cyclization precursor.

SUBMITTER: Williams BD

PROVIDER: S-EPMC4184459 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Total synthesis of (+)-18-epi-latrunculol A: development of a synthetic route.

Williams Brett D BD Smith Amos B AB

The Journal of organic chemistry 20140922 19

The evolution of an enantioselective total synthesis of (+)-18-epi-latrunculol A, a congener of the marine-sponge-derived latrunculins A and B, is reported. Key steps include a late-stage Mitsunobu macrolactonization to construct the 16-membered macrolactone, a mild Carreira alkynylation to unite the northern and southern hemispheres, a diastereoselective, acid-mediated δ-hydroxy enone cyclization/equilibration sequence, and a functional-group-tolerant cross-metathesis to access the enone cycliz ...[more]

PMID: 25243951

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