An asymmetric synthesis of the polyol fragment of the polyene macrolide antibiotic RK-397

被引:15
作者
Fu, Fan [1 ]
Loh, Teck-Peng [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
BORON ALDOL REACTIONS; DIELS-ALDER REACTION; CHIRAL SYNTHESIS; HOMOALLYLIC ALCOHOLS; ORGANIC-SYNTHESIS; 1,5-ASYMMETRIC INDUCTION; DIRECTED REDUCTION; METHYL KETONES; ALDEHYDES; ORGANOBORANES;
D O I
10.1016/j.tetlet.2009.03.019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly convergent and asymmetric synthesis of the C11-C31 polyol fragment of RK-397 as a single isomer is accomplished via a catalytic enantioselective hetero-Diels-Alder reaction and an intermolecular olefin cross-metathesis as key steps. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3530 / 3533
页数:4
相关论文
共 62 条
[1]   CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES [J].
BROWN, HC ;
RANDAD, RS ;
BHAT, KS ;
ZAIDLEWICZ, M ;
RACHERLA, US .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2389-2392
[2]   CHIRAL SYNTHESIS VIA ORGANOBORANES .25. B-(Z AND E)-CROTYLBIS-(2-ISOCARANYL)BORANES AS VALUABLE REAGENTS FOR THE ASYMMETRIC CROTYLBORATION OF ALDEHYDES [J].
BROWN, HC ;
RANDAD, RS .
TETRAHEDRON, 1990, 46 (13-14) :4457-4462
[5]   CHIRAL SYNTHESIS VIA ORGANOBORANES .21. ALLYLBORATION AND CROTYLBORATION OF ALPHA-CHIRAL ALDEHYDES WITH DIISOPINOCAMPHEYLBORON AS THE CHIRAL AUXILIARY [J].
BROWN, HC ;
BHAT, KS ;
RANDAD, RS .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1570-1576
[8]   CHIRAL SYNTHESIS VIA ORGANOBORANES .35. SIMPLE PROCEDURES FOR THE EFFICIENT RECYCLING OF THE TERPENYL CHIRAL AUXILIARIES AND CONVENIENT ISOLATION OF THE HOMOALLYLIC ALCOHOLS IN ASYMMETRIC ALLYLBORATION AND CROTYLBORATION OF ALDEHYDES [J].
BROWN, HC ;
RACHERLA, US ;
LIAO, Y ;
KHANNA, VV .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) :6608-6614
[9]  
BROWN KS, 1987, OXFORD MONOGRAPHS BI, V3, P19
[10]   Total synthesis of the polyene-polyol macrolide RK-397, featuring cross-couplings of alkynylepoxide modules [J].
Burova, SA ;
McDonald, FE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2495-2500