STEREOSELECTIVE SYNTHESIS OF BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-GAMMA-BUTYROLACTONES ON PYRANOSE TEMPLATES

被引:25
作者
ALABED, Y [1 ]
ALTEL, TH [1 ]
VOELTER, W [1 ]
机构
[1] UNIV TUBINGEN,INST PHYSIOL CHEM,PHYS BIOCHEM ABT,HOPPE SEYLER STR 4,W-7400 TUBINGEN 1,GERMANY
关键词
D O I
10.1016/0040-4020(93)80016-M
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of sugar derived epoxy triflates 1 and 2 or epoxy ketoses 11 and 12 with ester or acid enolates followed by acid-catalyzed ring closure affords poly-substituted chiral butenolides in excellent yields.
引用
收藏
页码:9295 / 9306
页数:12
相关论文
共 28 条
[1]  
ALABED Y, 1992, TETRAHEDRON LETT, V33, P3305
[2]   INTRAMOLECULAR FREE-RADICAL CYCLIZATIONS ONTO ENOL ETHERS - A GENERAL-SYNTHESIS OF ALPHA-ALKYL-BETA-OXY-GAMMA-BUTYROLACTONES AND ALPHA-METHYLENE-BETA-OXY-GAMMA-BUTYROLACTONES [J].
BEGLEY, MJ ;
LADLOW, M ;
PATTENDEN, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05) :1095-1106
[3]   SYNTHESIS OF ETHISOLIDE, ISOAVENACIOLIDE, AND AVENACIOLIDE [J].
BURKE, SD ;
PACOFSKY, GJ ;
PISCOPIO, AD .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2228-2235
[4]   STUDIES ON STRUCTURALLY SIMPLE ALPHA,BETA-BUTENOLIDES .2. (-)-(S)-GAMMA-HYDROXYMETHYL-ALPHA,BETA-BUTENOLIDE AND DERIVATIVES FROM D-RIBONOLACTONE EFFICIENT SYNTHESIS OF (-)-RANUNCULIN [J].
CAMPS, P ;
CARDELLACH, J ;
FONT, J ;
ORTUNO, RM ;
PONSATI, O .
TETRAHEDRON, 1982, 38 (15) :2395-2402
[5]   STUDIES ON STRUCTURALLY SIMPLE ALPHA,BETA-BUTENOLIDES .1. NEW SYNTHESES OF RACEMIC GAMMA-HYDROXYMETHYL-ALPHA,BETA-BUTENOLIDE AND DERIVATIVES [J].
CARDELLACH, J ;
ESTOPA, C ;
FONT, J ;
MORENOMANAS, M ;
ORTUNO, RM ;
SANCHEZFERRANDO, F ;
VALLE, S ;
VILAMAJO, L .
TETRAHEDRON, 1982, 38 (15) :2377-2394
[6]   TOTAL SYNTHESIS OF (+/-)-GINKGOLIDE-B [J].
COREY, EJ ;
KANG, M ;
DESAI, MC ;
GHOSH, AK ;
HOUPIS, JN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :649-651
[7]  
FRASERREID B, 1987, J ORG CHEM, V52, P4505, DOI 10.1021/jo00229a014
[8]   DIPYRANOSIDE PRECURSORS FOR ANSAMYCINS - PYRANOSIDIC HOMOLOGATION .5. [J].
FRASERREID, B ;
MAGDZINSKI, L ;
MOLINO, BF ;
MOOTOO, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4495-4504
[9]  
GRIECO PA, 1974, J ORG CHEM, V39, P120, DOI 10.1021/jo00915a036
[10]  
GRIECO PA, 1975, SYNTHESIS-STUTTGART, P67