Synthesis of Substituted 1-Thiocyanatobutadienes and their Application in a Diels-Alder /[3,3] Sigmatropic Rearrangement Tandem Reaction

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-thiocyanatobutadienes, is reported. Enolisation of this enone was studied to find the optimal conditions to get the desired 1-thiocyanatobutadienes with good Z-selectivit

2,2′-[(2S*,6R*)-Piperidine-2,6-di­yl]­di­pro­pan-2-ol

In the title compound, C11H23NO2, the piperidine ring has a chair conformation. The two hy­droxy H atoms are disordered over two positions with fixed occupancy ratios of 0.57:0.43 and 0.63:0.37. In the mol­ecule, there are two short N—H⋯O inter­actions. In the crystal, four symmetry-related mol­ecules are linked by O—H⋯O hydrogen bonds to form a cage-like arrangement, centered about the point of inter­section of three twofold axes. These cages stack along the [100] direction