Boc2O mediated macrolactonisation:: Formal chemoenzymatic synthesis of macrolide antibiotic (-) A26771B

被引:15
作者
Nagarajan, M [1 ]
机构
[1] Indian Inst Chem Technol, Hyderabad 500007, Andhra Pradesh, India
关键词
macrolides; hydroxylation; enzyme reactions; lactonisation;
D O I
10.1016/S0040-4039(98)02567-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient stereocontrolled, formal chemoenzymatic synthesis of macrolide antibiotic A26771B (1) using the improved macrolactonisation reagent, Boc(2)O-iPr(2) NEt/pyrrolidinopyridine(4-PP) is reported (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1207 / 1210
页数:4
相关论文
共 20 条
[1]   Enzymatic hydrolysis of acylals. A promising route to chiral aldehydes [J].
Angelis, YS ;
Smonou, I .
TETRAHEDRON LETTERS, 1997, 38 (46) :8109-8112
[2]   Enantioselectivity and diastereoselectivity in the hydrolysis of acylals and structurally related esters of secondary alcohols with Candida rugosa lipase. [J].
Angelis, YS ;
Smonou, I .
TETRAHEDRON LETTERS, 1998, 39 (18) :2823-2826
[3]   BIOSYNTHESES OF ANTIBIOTIC A26771B BY PENICILLIUM-TURBATUM AND DEHYDROCURVULARIN BY ALTERNARIA-CINERARIAE - COMPARISON OF STEREOCHEMISTRY OF POLYKETIDE AND FATTY-ACID ENOYL THIOL ESTER REDUCTASES [J].
ARAI, K ;
RAWLINGS, BJ ;
YOSHIZAWA, Y ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3391-3399
[4]   SYNTHESIS OF MACROCYCLIC LACTONES APPLYING INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION - SYNTHESIS OF (+/-)-A26771B [J].
ASAOKA, M ;
ABE, M ;
MUKUTA, T ;
TAKEI, H .
CHEMISTRY LETTERS, 1982, (02) :215-218
[5]   INTRAMOLECULAR PALLADIUM-CATALYZED CROSS COUPLING - A ROUTE TO GAMMA-OXO-ALPHA,BETA-UNSATURATED MACROCYCLES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
RAMCHARITAR, SH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) :940-942
[6]   SYNTHESIS OF MACROCYCLIC ALPHA,BETA-UNSATURATED GAMMA-OXOLACTONES BY RING-ENLARGEMENT REACTIONS - A NEW PATH TO THE MACROCYCLIC LACTONE ANTIBIOTIC-A-26771-B [J].
BIENZ, S ;
HESSE, M .
HELVETICA CHIMICA ACTA, 1987, 70 (05) :1333-1340
[7]  
CELMER W D, 1971, Pure and Applied Chemistry, V28, P413, DOI 10.1351/pac197128040413
[8]   A SHORT-STEP SYNTHESIS OF ANTIBIOTIC-A26771B UTILIZING THE RING-OPENING REACTION OF BETA-ETHYNYL-BETA-PROPIOLACTONE [J].
FUJISAWA, T ;
OKADA, N ;
TAKEUCHI, M ;
SATO, T .
CHEMISTRY LETTERS, 1983, (08) :1271-1272
[9]  
HASE TA, 1979, TETRAHEDRON LETT, V20, P2633
[10]   RAPID ESTERIFICATION BY MEANS OF MIXED ANHYDRIDE AND ITS APPLICATION TO LARGE-RING LACTONIZATION [J].
INANAGA, J ;
HIRATA, K ;
SAEKI, H ;
KATSUKI, T ;
YAMAGUCHI, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (07) :1989-1993