Stereoselective synthesis of the C1-C29 part of amphidinol 3

Takeshi Tsuruda, Makoto Ebine, Aya Umeda, Tohru Oishi

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18 Citations (Scopus)

Abstract

Stereoselective synthesis of the C1-C29 part of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asymmetric reduction to form the C9-C10 and C14-C15 bonds, respectively. The C21-C29 part was synthesized via successive cross metathesis and oxa-Michael addition sequence to construct the 1,3-diol system at C25 and C27 and Brown asymmetric crotylation to introduce the stereogenic centers at C23 and C24. Coupling of the C1-C20 and C21-C29 parts was achieved by Julia-Kocienski olefination and regio- and stereoselective dihydroxylation of the C20-C21 double bond in the presence of the C4-C5 and C8-C9 double bonds to afford the C1-C29 part of AM3.

Original languageEnglish
Pages (from-to)859-871
Number of pages13
JournalJournal of Organic Chemistry
Volume80
Issue number2
DOIs
Publication statusPublished - Jan 16 2015

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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