863191-54-2Relevant academic research and scientific papers
Synthesis of substituted 1-thiocyanatobutadienes and their application in a Diels-Alder/[3,3] sigmatropic rearrangement tandem reaction
Lanaspeze, Sebastien,Neier, Reinhard
, p. 597 - 607 (2005)
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-thiocyanatobutadienes, is reported. Enolisation of this enone was studied to find the optimal conditions to get the desired 1-thiocyanatobutadienes with good Z-selectivity. Springer-Verlag 2005.
