Stereodivergent syntheses of conduramines and aminocyclitols

被引：31
作者：
Alegret, Carlos
Benet-Buchholz, Jordi
Riera, Antoni
机构：
[1] Univ Barcelona, URSA, PCB, IRB, E-08028 Barcelona, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
[3] Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 14期
关键词：
D O I：
10.1021/ol061022e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] The diastereomers of 6-amino-cyclohex-3-ene- 1,2-diols 1 (4-deoxy-3-conduramines), key building blocks for the syntheses of a large range of natural products, have been enantioselectively prepared. Diastereoselective dihydroxylation of the compounds provided a new family of aminocyclitols 2 (deoxyinosamines). The key reactions of our syntheses are Sharpless catalytic asymmetric epoxidation, diastereoselective addition of vinylmetal reagents to the aldehydes, and ring-closing metathesis (RCM).
引用
收藏
页码：3069 / 3072
页数：4
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