New Piperidinic Synthons via Ring Contraction. Formal Synthesis of (±)-Perhydrohistrionicotoxin

P Duhamel, M Kotera, T Monteil

Index: Duhamel, Pierre; Kotera, Mitsuharu; Monteil, Thierry Bulletin of the Chemical Society of Japan, 1986 ,  vol. 59,  # 7  p. 2353 - 2355

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Citation Number: 10

Abstract

The 2, 2-bifunctionalized piperidines 6 and 10 were obtained via ring contraction of the seven-membered heterocyclic enamino aldehyde 5 in nearly quantitative yield. The synthesis of 1-benzyl-1-azaspiro [5.5] undec-7-en-9-one 9 (a formal precursor of perhydrohistrionicotoxin 1b) in 3 steps from the piperidinedialdehyde monoacetal 6, is reported.