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

来源：

TETRAHEDRON | 1993年 / 49卷 / 41期

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

页码：9295 / 9306

页数：12

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
BEGLEY, MJ
LADLOW, M
PATTENDEN, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (05): : 1095 - 1106
[3] SYNTHESIS OF ETHISOLIDE, ISOAVENACIOLIDE, AND AVENACIOLIDE
BURKE, SD
PACOFSKY, GJ
PISCOPIO, AD
[J]. 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
CAMPS, P
CARDELLACH, J
FONT, J
ORTUNO, RM
PONSATI, O
[J]. 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
CARDELLACH, J
ESTOPA, C
FONT, J
MORENOMANAS, M
ORTUNO, RM
SANCHEZFERRANDO, F
VALLE, S
VILAMAJO, L
[J]. TETRAHEDRON, 1982, 38 (15) : 2377 - 2394
[6] TOTAL SYNTHESIS OF (+/-)-GINKGOLIDE-B
COREY, EJ
KANG, M
DESAI, MC
GHOSH, AK
HOUPIS, JN
[J]. 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.
FRASERREID, B
MAGDZINSKI, L
MOLINO, BF
MOOTOO, DR
[J]. 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

← 1 2 3 →