SYNTHESIS OF HYDROXYETHYLENE ISOSTERES OF THE TRANSITION-STATE OF THE HIV PROTEASE-CATALYZED PHE-PRO HYDROLYSIS - REACTION OF 2-[(BOC)AMINO]-1-(2'-OXOCYCLOPENTYL)-3-PHENYLPROPANOLS WITH DIETHYL PHOSPHOROCYANIDATE AND LITHIUM CYANIDE FOLLOWED BY SAMARIUM IODIDE

被引：13

作者：

KONIECZNY, MT ^{[1
]}

TOMA, PH ^{[1
]}

CUSHMAN, M ^{[1
]}

机构：

[1] PURDUE UNIV,DEPT MED CHEM & PHARMACOGNOSY,W LAFAYETTE,IN 47907

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 17期

关键词：

D O I：

10.1021/jo00069a024

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of cyclopentanone enolate (7) with BoC-L-Phenylalaninal (6) afforded a mixture of four aldol products 5a-d in a 3:3:1:1 ratio. Reaction of 5a with diethyl phosphorocyanidate followed by samarium iodide reduction afforded lactone 13a and phosphate 12. The structure of 12 was confirmed by X-ray crystallography. Deprotection of 13a gave (1R,1'S,2S,2'S)-2-(2'-amino-1'-hydroxy-3'-phenylpropyl)cyclopentanecarboxylic acid lactone (14a), which was transformed to a crystalline lactam 15a under basic conditions. The structure of 15a was also confirmed by X-ray analysis.

引用

页码：4619 / 4624

页数：6

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