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

…, F Ozaki, N Shirakata, Y Tamaoka, H Yamamoto…

Index: Tsunoda; Ozaki; Shirakata; Tamaoka; Yamamoto; Ito Tetrahedron Letters, 1996 , vol. 37, # 14 p. 2463 - 2466

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Citation Number: 76

Abstract

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.