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Communication | Special issue | Vol 69, No. 1, 2006, pp.91-98
Published online, 21st July, 2006
DOI: 10.3987/COM-06-S(O)23
■ Convergent Synthesis of the CDEF Ring Fragment of Yessotoxin via α-Cyano Ethers

Tohru Oishi,* Miho Suzuki, Koji Watanabe, and Michio Murata

*Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan

Abstract

The synthesis of the CDEF ring fragment of yessotoxin, a marine ladder polyether, has been achieved. Union of three components, the C ring aldehyde, the F ring diol, and trimethylsilyl cyanide, was accomplished by treatment with Sc(OTf)3 to afford the α-cyano ether both in stepwise and one-pot reactions. The DE ring system was constructed through a ring closing metathesis reaction and reductive etherification sequence.