Asymmetric Syntheses of 1-Deoxy-6,8a-di-epi-castanospermine and 1-Deoxy-6-epi-castanospermine.

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 of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.

Citation

Hwayoung Yun, Jongmin Kim, Jaehoon Sim, Sujin Lee, Young Taek Han, Dong-Jo Chang, Dae-Duk Kim, Young-Ger Suh. Asymmetric Syntheses of 1-Deoxy-6,8a-di-epi-castanospermine and 1-Deoxy-6-epi-castanospermine. The Journal of organic chemistry. 2012 Jun 15;77(12):5389-93

PMID: 22612538

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