Tetrahedron letters

Tin-assisted cyclization for chiral cyclohexane synthesis, an alternative route to (−)-tetrodotoxin skeleton

M Bamba, T Nishikawa, M Isobe

文献索引：Bamba, Makoto; Nishikawa, Toshio; Isobe, Minoru Tetrahedron Letters, 1996 , vol. 37, # 45 p. 8199 - 8202

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被引用次数: 21

摘要

A carbon framework including chiral cyclohexane was synthesized as a possible intermediate for tetrodotoxin. The key steps were electrocyclization of the precursor triene derivatives. Smooth cyclization resulted especially with tributyltin derivative due to an attractive interaction with the 2-oxygen function. The corresponding triethylsilyl derivative scarcely reacted due to rather repulsive interaction.