有機触媒を用いた不斉アジリジン化を鍵反応とする(-)-Agelastatin Aの全合成

抄録

Agelastatin A is an unusual tetracyclic alkaloid isolated by Pietra's group in 1993. The highly complex structure, coupled with its remarkable biological activities, has made agelastatin A an attractive target for total synthesis. In this symposium, we will report a highly efficient formal total synthesis of agelastatin A. In this study we have discovered the asymmetric aziridination of cyclic enones catalyzed by primary-secondary chiral diamines, which can be simply prepared from commercially available 1,2-diphenylethylenediamine. The chiral keto aziridine 2 derived from 2-cyclopenten-1-one could efficiently convert to the Ichikawa's chiral intermediate 1 by 6 steps, including a DBU catalyzed one-pot silylation-selenylation procedure, and a regioselective aziridine-opening by an azide anion as key steps.