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Synlett 2010(6): 982-986  
DOI: 10.1055/s-0029-1219540
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Exploratory Studies en Route to 5-Alkyl-Hyacinthacines: Synthesis of 5-epi-(-)-Hyacinthacine A3 and (-)-Hyacinthacine A3

Xiang-Guo Hua,b, Yue-Mei Jiaa, Junfeng Xianga, Chu-Yi Yu*a
a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
Fax: +86 10 82616433; e-Mail: yucy@iccas.ac.cn;
b Graduate University of The Chinese Academy of Sciences, Beijing 100049, P. R. of China
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Publication History

Received 22 December 2009
Publication Date:
23 February 2010 (online)

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Abstract

Synthesis of 5-epi-(-)-hyacinthacine A3 and (-)-hyacinthacine A3 has been achieved from the d-xylose-derived polyhydroxylated cyclic nitrone. Our synthetic strategy is potentially general and flexible for the synthesis of both epimers of 5-alkyl-­hyacinthacines.

Key words

nitrone - α-amino nitrile - iminosugars - polyhydroxylated pyrrolizidine - hyacinthacine

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25

The crystal structure of 19 has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number: CCDC 756239.