An Efficient Approach to the Synthesis of Ethyl Esters of 2,6-Anhydro-3-Deoxy-D-GlucoAnd D-Allo-Heptanoates
作者:
Lian-Sheng Li,
Yikang Wu,
Yu-Lin Wu,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1999)
卷期:
Volume 18,
issue 9
页码: 1067-1077
ISSN:0732-8303
年代: 1999
DOI:10.1080/07328309908544055
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
An efficient synthesis of analogues of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) is described. The route exploits a previously published highly double-stereoselective hetero Diels-Alder reaction catalyzed by a chiral salenCo(II) complex. Asymmetric dihydroxylation followed by selective reduction leads to stereoselective introduction of hydroxy groups at C-4 and C-5. Oxidative cleavage of the C-6 side-chain,in situreduction of the resulting aldehyde and deprotection afford the desired targets, which may be useful precursors to the simple analogues of the anti-influenza agent GG167.
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