Asymmetric Syntheses of 1-Deoxy-6,8a-di-epi-castanospermine and 1-Deoxy-6-epi-castanospermine
作者： Hwayoung Yun , Jongmin Kim , Jaehoon Sim , Sujin Lee , Young Taek Han
DOI: 10.1021/JO300309Z
关键词:
摘要: Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature our unique includes the stereoselective introduction C-3 C-4 hydroxyl groups utilizing aza-Claisen rearrangement-induced ring expansion 1-acyl-2-alkoxyvinyl pyrrolidine a substrate-controlled transannulation resulting azoninone intermediate.
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