Synthetic studies toward astins A, B and C.: Efficient syntheses of cis-3,4-dihydroxyprolines and (-)-(3S,4R)-dichloroproline esters

被引：62

作者：

Schumacher, KK

Jiang, JJ

Joullié, MM ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

[2] Abbott Labs, Abbott Pk, IL 60064 USA

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 01期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0957-4166(97)00617-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Efficient syntheses of the esters of cis-3,4-dihydroxyprolines and the first synthesis of the ester of the rare amino acid (-)-(3S,4R)-dichloroproline from trans-4-hydroxy-L-proline are presented. The synthetic route provides easy access to several substituted prolines and cis-hydroxylated proline esters. Various types of biological activities have been associated with these substituted prolines. The role of (-)-(3S,4R)-dichloroproline in astins A, B and C is under investigation. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：47 / 53

页数：7

相关论文

共 86 条

[1] SYNTHESIS OF CIS AND TRANS ISOMERS OF 4-CHLORO-L-PROLINE 4-BROMO-L-PROLINE AND 4-AMINO-L-PROLINE [J].

ANDREATTA, RH ;

NAIR, V ;

ROBERTSON, AV ;

SIMPSON, WRJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1967, 20 (07) :1493-+

[2]

ARAKAWA Y, 1991, CHEM PHARM BULL, V39, P2219

[3] N-ALKYLATED NITROGEN-IN-THE-RING SUGARS - CONFORMATIONAL BASIS OF INHIBITION OF GLYCOSIDASES AND HIV-1 REPLICATION [J].

ASANO, N ;

KIZU, H ;

OSEKI, K ;

TOMIOKA, E ;

MATSUI, K ;

OKAMOTO, M ;

BABA, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (13) :2349-2356

[4] NITROGEN-IN-THE-RING PYRANOSES AND FURANOSES - STRUCTURAL BASIS OF INHIBITION OF MAMMALIAN GLYCOSIDASES [J].

ASANO, N ;

OSEKI, K ;

KIZU, H ;

MATSUI, K .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (22) :3701-3706

[5] Homonojirimycin isomers and glycosides from Aglaonema treubii [J].

Asano, N ;

Nishida, M ;

Kizu, H ;

Matsui, K ;

Watson, AA ;

Nash, RJ .

JOURNAL OF NATURAL PRODUCTS, 1997, 60 (02) :98-101

[6]

AUSTIN GN, 1987, TETRAHEDRON, V43, P3095

[7] SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET [J].

BAIRD, PD ;

DHO, JC ;

FLEET, GWJ ;

PEACH, JM ;

PROUT, K ;

SMITH, PW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08) :1785-1791

[8] SUBSTRATE-SPECIFICITY OF PROLINE 4-HYDROXYLASE - CHEMICAL AND ENZYMATIC-SYNTHESIS OF 2S,3R,4S-EPOXYPROLINE [J].

BALDWIN, JE ;

FIELD, RA ;

LAWRENCE, CC ;

LEE, V ;

ROBINSON, JK ;

SCHOFIELD, CJ .

TETRAHEDRON LETTERS, 1994, 35 (26) :4649-4652

[9] THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE [J].

BASHYAL, BP ;

CHOW, HF ;

FELLOWS, LE ;

FLEET, GWJ .

TETRAHEDRON, 1987, 43 (02) :415-422

[10] SYNTHESIS OF THE ALPHA-MANNOSIDASE INHIBITORS SWAINSONINE [(1S, 2R, 8R, 8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE] AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL FROM MANNOSE [J].

BASHYAL, BP ;

FLEET, GWJ ;

GOUGH, MJ ;

SMITH, PW .

TETRAHEDRON, 1987, 43 (13) :3083-3093

← 1 2 3 4 5 6 7 8 9 →