Synlett

A Short Formal Synthesis of (±)-Perhydrohistrionicotoxin

A Deyine, JM Poirier, P Duhamel

Index: Deyine, Abdallah; Poirier, Jean-Marie; Duhamel, Pierre Synlett, 2008 , # 2 p. 260 - 262

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Citation Number: 4

Abstract

Abstract The reaction of a silyl enol ether bearing a nitrogen atom with a hemiacetal vinylog in the presence of a catalytic amount of boron trifluoride etherate led to the corresponding ketoaldehyde. The cyclisation of the ketoaldehyde into azaspiroenone and nitrogen deprotection was performed in basic medium. The N-benzylation of this enone gave the known key intermediate of total synthesis of (±)-perhydrohistrionicotoxin.

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