Formation of heterocycles by the Mitsunobu reaction. Stereoselective ynthesis of (+)-α-skytanthine

Article abstract of DOI:10.1016/0040-4039(96)00319-X

Cyanomethylenetributylphosphorane was shown to mediate the dehydrocyclization of diols and amino alcohols to give the corresponding 6-membered O- and N-heterocycles in 90% or better yields. Using the reaction as a key step, (+)-α-skytanthine, a unique mono terpene alkaloid, was synthesized stereoselectively.