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

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 12期

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).

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页码：1581 / 1584

页数：4

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