Tin-assisted cyclization for chiral cyclohexane synthesis, an alternative route to (−)-tetrodotoxin skeleton
M Bamba, T Nishikawa, M Isobe
Index: Bamba, Makoto; Nishikawa, Toshio; Isobe, Minoru Tetrahedron Letters, 1996 , vol. 37, # 45 p. 8199 - 8202
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Citation Number: 21
Abstract
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.
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