Ling Zhou, Jie Chen, Xiao-Ping Cao
May 1, 2007
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Journal
Synthesis
Abstract
The two partially protected pyrrolidines (2 R,3 S,4 R,5 S)- and (2 R,3 S,4 R,5 R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-5-[( TERT-butyldimethylsiloxy)methyl]pyrrolidine were synthesized from D-glucose as precursor in the stereoselective synthesis of hyacinthacines. The key strategies were the ring opening of the sugar epoxide with sodium azide to convert the configuration at C-2 and C-3 of D-glucose and simultaneous reduction and intramolecular cyclization. 5- EPI-Hyacinthacine A 4 was synthesized from the (2 R,3 S,4 R,5 S)-pyrrolidine by Wittig reaction and cyclization.