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■ Rearrangement-Ring Expansion Reaction of Functionalized Cyclic Ethers. Stereoselective Synthesis of the ST- and XY-Ring Systems of Maitotoxin

Kazuo Nagasawa, Nobuyuki Hori, Ryuichi Shiba, and Tadashi Nakata*

*The Institute of Physical and Chemical Research, Wako-shi, Saitama 351-0198, Japan

Abstract

The rearrangement of 6-membered ethers having olefinic functional groups on the C2-side chain with Zn(OAc)₂ proceeded smoothly with ring expansion to give the 7-membered ethers. The 5,7-membered ether, prepared from the 7-membered ether, was again subjected to the rearrangement-ring expansion reaction to give the 6,7-membered ether, corresponding to the ST- and XY-ring systems of maitotoxin.