doi: 10.1021/ol902778y.
Total synthesis of (-)-exiguolide
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- PMID: 20063897
- DOI: 10.1021/ol902778y
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Total synthesis of (-)-exiguolide
Org Lett.
.
Abstract
Total synthesis of (-)-exiguolide, the natural enantiomer, has been accomplished for the first time. The bis(tetrahydropyran) subunit was efficiently synthesized via consecutive olefin cross-metathesis/intramolecular oxa-conjugate addition/reductive etherification. Construction of the 20-membered macrocycle was achieved by Yamaguchi macrolactonization. Stereoselective introduction of the (E,Z,E)-triene side chain via Suzuki-Miyaura coupling completed the total synthesis.
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