Total synthesis of methyl sarcophytoate, a marine natural biscembranoid

Takahiro Ichige, Yusuke Okano, Naoki Kanoh, Masaya Nakata

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

(Chemical Equation Presented) The total synthesis of methyl sarcophytoate (1), a marine natural biscembranoid, has been achieved by the thermal Diels-Alder reaction between the 14-membered dienophile unit, methyl sarcoate (2), and the 14-membered diene unit 64. Methyl sarcoate (2) was prepared using n-BuLi-Bu2Mg-mediated dithiane coupling, Kosugi-Migita-Stille coupling, and Grubbs ring-closing metathesis. The diene unit 64 was prepared using Sharpless asymmetric epoxidation, Grubbs ring-closing metathesis, 6-exo-tet epoxide opening, and n-BuLi-Bu2Mg-mediated Ito-Kodama cyclization. The final Diels-Alder reaction between 2 and 64 proceeded with high site, endo/exo, π-face, and regioselectivities. During this reaction, partial E → Z isomerization at the C4 position was observed.

Original languageEnglish
Pages (from-to)230-243
Number of pages14
JournalJournal of Organic Chemistry
Volume74
Issue number1
DOIs
Publication statusPublished - 2009 Jan 2

ASJC Scopus subject areas

  • Organic Chemistry

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