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

1996; Elsevier BV; Volume: 37; Issue: 14 Linguagem: Inglês

10.1016/0040-4039(96)00319-x

1873-3581

Tetsuto Tsunoda, Fumie Ozaki, Nozomi Shirakata, Yuki Tamaoka, Hidetoshi Yamamoto, Shô Itô,

Cyclopropane Reaction Mechanisms

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.