Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0040-4020(01)86601-1
Title: Enantiomeric synthesis of polyhydroxylated indolizidine analogues related to castanospermine: 1-Deoxy-7-epicastanospermine and 1,7-dideoxy-7-fluorocastanospermine
Authors: Lee, C.-K. 
Sim, K.Y. 
Zhu, J.
Issue Date: 1992
Source: Lee, C.-K., Sim, K.Y., Zhu, J. (1992). Enantiomeric synthesis of polyhydroxylated indolizidine analogues related to castanospermine: 1-Deoxy-7-epicastanospermine and 1,7-dideoxy-7-fluorocastanospermine. Tetrahedron 48 (39) : 8541-8544. ScholarBank@NUS Repository. https://doi.org/10.1016/S0040-4020(01)86601-1
Abstract: (6S,7S,8R,8aR)-6,7,8-Trihydroxyindolizidine (i) and its (7R)-deoxyfluoro analogue (2) was synthesised from 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene- α-D-gluco-octose (3). The key step is an oxidation-reduction sequence. Introduction of a fluoro substituent at C-3 (6) was readily effected by displacement of the 3-trifluoromethanesulfonyl (triflate) group with tris-(dimethylamino)-sulfonium-difluorotrimethylsilicate (TASF).
Source Title: Tetrahedron
URI: http://scholarbank.nus.edu.sg/handle/10635/76094
ISSN: 00404020
DOI: 10.1016/S0040-4020(01)86601-1
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