A PRACTICAL SYNTHESIS OF THE DIHYDROXYETHYLENE DIPEPTIDE ISOSTERE, (2S,3R,4S) 2-[(TERT-BUTYLOXYCARBONYL)AMINO]-1-CYCLOHEXYL-3,4-DIHYDROXY-6-METHYLHEPTANE, FROM D-ISOASCORBIC ACID

被引:16
作者
BAKER, WR
CONDON, SL
机构
[1] Pharmaceutical Products Division, Abbott Laboratories, Abbott Park, IL 60064, One Abbott Park Road
关键词
D-ISOASCORBIC ACID; DIHYDROXYETHYLENE DIPEPTIDE ISOSTERE; STEREOSELECTIVE ORGANOMETALLIC ADDITION REACTION;
D O I
10.1016/S0040-4039(00)91679-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The N-Boc dihydroxyethylene dipeptide isostere 7 and its N-Boc 3-(thiazol-4-yl)alanyl derivative 8 were synthesized, without purification of intermediates, from (4S,5R)-2,2-dimethyl-4-(2-methylpropyl)-5-hydroxymethyl-1,3-dioxolane (3b), in 24 and 32% overall yield, respectively. Alcohol 3b was readily prepared from inexpensive and commerically available D-isoascorbic acid in four steps. The synthesis featured a stereoselective addition of cyclohexylmethyllithium to the dimethyl hydrazone of (4S,5S)-2,2-dimethyl-4-(2-methylpropyl)-5-formyl-1,3-dioxolane (4).
引用
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页码:1581 / 1584
页数:4
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