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Polyketide assembly by alkene-alkyne reductive cross-coupling: spiroketals through the union of homoallylic alcohols.

ABSTRACT: A reaction sequence composed of regioselective formal hydroalkynylation, reductive ene-yne cross-coupling, and oxidative cyclization has been developed to prepare stereochemically dense spiroketals. Overall, the chemistry defines a three-component coupling process for the union of two homoallylic alcohol-based substrates with trimethylsilylacetylene.

SUBMITTER: Canterbury DP

PROVIDER: S-EPMC2892691 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature

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Polyketide assembly by alkene-alkyne reductive cross-coupling: spiroketals through the union of homoallylic alcohols.

Canterbury Daniel P DP Micalizio Glenn C GC

Journal of the American Chemical Society 20100601 22

A reaction sequence composed of regioselective formal hydroalkynylation, reductive ene-yne cross-coupling, and oxidative cyclization has been developed to prepare stereochemically dense spiroketals. Overall, the chemistry defines a three-component coupling process for the union of two homoallylic alcohol-based substrates with trimethylsilylacetylene. ...[more]

PMID: 20476790

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