Total synthesis of (-)-exiguolide

Haruhiko Fuwa; Makoto Sasaki

doi:10.1021/ol902778y

Total synthesis of (-)-exiguolide

Haruhiko Fuwa, Makoto Sasaki

LIF - Molecular and Chemical Life Science

Tohoku University

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

Abstract

[Chemical equation presented] 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 macrolactonizatlon. Stereoselective introduction of the (E,Z,E)-triene side chain via Suzuki-Miyaura coupling completed the total synthesis.

Original language	English
Pages (from-to)	584-587
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	3
DOIs	https://doi.org/10.1021/ol902778y
Publication status	Published - 2010 Feb 5

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10.1021/ol902778y

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Total synthesis of (-)-exiguolide

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