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Synthesis 2007(9): 1359-1365  
DOI: 10.1055/s-2007-966022
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of Functionalized Pyrrolidines and 5-epi-Hyacinthacine A4 from d-Glucose

Ling Zhou, Jie Chen, Xiao-Ping Cao*
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China
Fax: +86(931)8912582; e-Mail: caoxplzu@163.com;
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Publication History

Received 19 January 2007
Publication Date:
18 April 2007 (online)

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Abstract

The two partially protected pyrrolidines (2R,3S,4R,5S)- and (2R,3S,4R,5R)-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 A4 was synthesized from the (2R,3S,4R,5S)-pyrrolidine by Wittig reaction and cyclization.

Key words

azasugars - chiral pool - hyacinthacine - pyrrolidines - ring opening