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Convergent route to the spirohexenolide macrocycle.

ABSTRACT: Using key functional dissections, the synthesis of spirohexenolides is examined through a three-component strategy that features a 1,2-addition to couple tetronate and aldehyde components forming the C2-C3 bond and a Stille coupling to install the third sulfone-containing component. The macrocycle is completed by an intramolecular Julia-Kocienski reaction to form the C10-C11 trans-disubstituted olefin. Application of this strategy is described in progress toward the synthesis of (±)-spirohexenolide B.

SUBMITTER: Jones BD

PROVIDER: S-EPMC2956428 | biostudies-literature | 2010 Oct

REPOSITORIES: biostudies-literature

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Convergent route to the spirohexenolide macrocycle.

Jones Brian D BD La Clair James J JJ Moore Curtis E CE Rheingold Arnold L AL Burkart Michael D MD

Organic letters 20101001 20

Using key functional dissections, the synthesis of spirohexenolides is examined through a three-component strategy that features a 1,2-addition to couple tetronate and aldehyde components forming the C2-C3 bond and a Stille coupling to install the third sulfone-containing component. The macrocycle is completed by an intramolecular Julia-Kocienski reaction to form the C10-C11 trans-disubstituted olefin. Application of this strategy is described in progress toward the synthesis of (±)-spirohexenol ...[more]

PMID: 20849075

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