Monatshefte für Chemie/Chemical Monthly

Synthesis of substituted 1-thiocyanatobutadienes and their application in a Diels-Alder/[3, 3] sigmatropic rearrangement tandem reaction

S Lanaspèze, R Neier

Index: Lanaspeze, Sebastien; Neier, Reinhard Monatshefte fur Chemie, 2005 , vol. 136, # 4 p. 597 - 607

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Citation Number: 2

Abstract

Summary. The retrosynthetic analysis of Ibogamine, a natural psychotropic alkaloid with exceptional anti-addictive properties found in both enantiomeric forms, requires an efficient access to a racemic cyclohexene. This cyclohexene can be obtained via the sequence Diels- Alder/[3, 3] sigmatropic rearrangement reaction starting from substituted 1- thiocyanatobutadienes. An efficient synthesis of the enone, a stable precursor of 1- ...