Citation: Xin-Yi Jiang, Xiu-Hua Xu, Feng-Ling Qing. Design and concise synthesis of gem-difluoromethylenated analogue of 7-epi-castanospermine[J]. Chinese Chemical Letters, ;2014, 25(8): 1115-1120. doi: 10.1016/j.cclet.2014.04.018 shu

Design and concise synthesis of gem-difluoromethylenated analogue of 7-epi-castanospermine

1.
a Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai 200032, China;
2.
b College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China

Corresponding author: Feng-Ling Qing,
Received Date: 20 February 2014
Available Online: 10 April 2014
Fund Project: We thank the National Natural Science Foundation of China (Nos. 21272036, 21332010) (Nos. 21272036, 21332010)the National Basic Research Program of China (No. 2012CB21600) for funding this work. (No. 2012CB21600)

A novel gem-difluoromethylenated castanospermine analogue B was designed and synthesized, starting from 3-bromo-3,3-difluoropropene and L-(-)-malic acid. The key steps involve substitution cyclization reaction and RCM reaction to construct the aza fused bicyclic framework.
- Indolizidine,
- Castanospermine,
- gem-Difluoromethylene,
- Cyclization,
- Dihydroxylation
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