Synthetic Studies on Maitotoxin. 2. Stereoselective Synthesis of the WXYZA′-Ring System

Org. Lett., 10 (9), 1679–1682, 2008. 10.1021/ol800268c
Web Release Date: April 8, 2008

Synthetic Studies on Maitotoxin. 2. Stereoselective Synthesis of the WXYZA′-Ring System

Masayuki Morita,^†^# Tasuku Haketa,^‡ Hiroyuki Koshino,^† and Tadashi Nakata^*^‡

RIKEN (The Institute of Physical and Chemical Research), 1-2 Hirosawa, Wako-shi, Saitama 351-0198, Japan, and Department of Chemistry, Faculty of Science, Tokyo University of Science, 1-3 Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan

nakata@rs.kagu.tus.ac.jp

Received February 6, 2008

Abstract:

The stereoselective synthesis of the WXYZA′-ring system of maitotoxin has been accomplished via a linear synthetic approach, in which key reactions were SmI₂-induced cyclization of β-alkoxyacrylate for the construction of the A′-, Y-, and X-rings and 6-endo cyclization of hydroxy vinylepoxide for that of the Z- and W-rings.

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