Practical synthesis of Abbott amino-diol: A core unit of the potent renin inhibitor Zankiren

被引：20

作者：

Chandrasekhar, S ^{[1
]}

Mohapatra, S ^{[1
]}

Yadav, JS ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India

来源：

TETRAHEDRON | 1999年 / 55卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(99)00148-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Abbott amino-diol (2S,3R, 4S)-2-amino-1-cyclohexyl-6-methyl heptane-3,4-diol 1, a main structural constituent of the orally active renin inhibitor Zankiren has been synthesized using Sharpless asymmetric aminohydroxylation as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4763 / 4768

页数：6

共 23 条

[1] A diastereoselective synthesis of (2S, 3R, 4S)-2-amino-1-cyclohexyl-6-methylheptane-3,4-diol, the Abbott aminodiol. [J].

Alexander, CW ;

Liotta, DC .

TETRAHEDRON LETTERS, 1996, 37 (12) :1961-1964

[2] DIPEPTIDE ISOSTERES .1. SYNTHESIS OF DIHYDROXYETHYLENE DIPEPTIDE ISOSTERES VIA DIASTEREOSELECTIVE ADDITIONS OF ALKYLLITHIUM REAGENTS TO N,N-DIMETHYLHYDRAZONES - PREPARATION OF RENIN AND HIV-1 PROTEASE INHIBITOR TRANSITION-STATE MIMICS [J].

BAKER, WR ;

CONDON, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3277-3284

[3] N-bromoacetamide - A new nitrogen source for the catalytic asymmetric aminohydroxylation of olefins [J].

Bruncko, M ;

Schlingloff, G ;

Sharpless, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14) :1483-1486

[4] A VERSATILE AND STEREOSPECIFIC SYNTHESIS OF A DIHYDROXYETHYLENE DIPEPTIDE ISOSTERE OF RENIN INHIBITORS FROM D-RIBOSE [J].

CHAN, MF ;

HSIAO, CN .

TETRAHEDRON LETTERS, 1992, 33 (25) :3567-3570

[5] Neighbouring group assisted sulfonamide cleavage of sharpless aminols under acetonation conditions [J].

Chandrasekhar, S ;

Mohapatra, S .

TETRAHEDRON LETTERS, 1998, 39 (07) :695-698

[6] RENIN INHIBITORS [J].

GREENLEE, WJ .

MEDICINAL RESEARCH REVIEWS, 1990, 10 (02) :173-236

[7]

GREENLEE WJ, 1987, PHARMACEUT RES, P4364

[8] Asymmetric synthesis of the Abbott amino dihydroxyethylene dipeptide isostere subunit [J].

Haddad, M ;

Larcheveque, M .

TETRAHEDRON LETTERS, 1996, 37 (26) :4525-4528

[9] DISCOVERY OF A PEPTIDE-BASED RENIN INHIBITOR WITH ORAL BIOAVAILABILITY AND EFFICACY [J].

KLEINERT, HD ;

ROSENBERG, SH ;

BAKER, WR ;

STEIN, HH ;

KLINGHOFER, V ;

BARLOW, J ;

SPINA, K ;

POLAKOWSKI, J ;

KOVAR, P ;

COHEN, J ;

DENISSEN, J .

SCIENCE, 1992, 257 (5078) :1940-1943

[10]

KOBAYASHI Y, 1992, CHEM PHARM BULL, V33, P3567

← 1 2 3 →