HIGHLY REGIOCONTROLLED AND STEREOCONTROLLED GLYOXYLATE-ENE REACTION WITH (HOMO)ALLYLIC ETHERS - REMARKABLE ALKOXY EFFECT IN REGIOCONTROL AND STEREOCONTROL

被引：37

作者：

MIKAMI, K

SHIMIZU, M

NAKAI, T

机构：

[1] Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 09期

关键词：

D O I：

10.1021/jo00009a003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regio- and stereocontrolled glyoxylate-ene reaction with allylic and homoallylic ethers has been developed, which allows regio- and stereospecific multifunctionalizations as highlighted by a short synthesis of (+/-)-avenaciolide.

引用

页码：2952 / 2953

页数：2

共 27 条

[1] SYNTHESIS OF BIS-GAMMA-LACTONES FROM DIACETONE GLUCOSE .4. OPTICALLY-ACTIVE AVENACIOLIDE AND ISOAVENACIOLIDE
ANDERSON, RC
FRASERREID, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24) : 4781 - 4786
[2] AVENACIOLIDE, AN ANTIFUNGAL LACTONE FROM ASPERGILLUS AVENACEUS
BROOKES, D
TIDD, BK
TURNER, WB
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1963, (NOV): : 5385 - &
[3] BROOKES D, 1967, AUST J CHEM, V18, P373
[4] C15H22O4 COMPOUND PRODUCED BY FUNGUS ASPERGILLUS FISCHERI VAR GLABER
ELLIS, JJ
VESONDER, RF
GLASS, CA
STODOLA, FH
[J]. NATURE, 1964, 203 (495) : 1382 - &
[5] ENE REACTION
HOFFMANN, HM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) : 556 - &
[6] DIASTEREOGENIC ADDITION OF CROTYLMETAL COMPOUNDS TO ALDEHYDES
HOFFMANN, RW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (08): : 555 - 566
[7] INHIBITION OF INFECTIVITY OF HUMAN-IMMUNODEFICIENCY-VIRUS BY OXETANOCIN
HOSHINO, H
SHIMIZU, N
SHIMADA, N
TAKITA, T
TAKEUCHI, T
[J]. JOURNAL OF ANTIBIOTICS, 1987, 40 (07) : 1077 - 1078
[8] A SHORT, STEREOCONTROLLED SYNTHESIS OF AVENACIOLIDE
KALLMERTEN, J
GOULD, TJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (07) : 1128 - 1131
[9] CARBONYL ENE REACTION WITH VINYLSILANES - SILICON AS A CONTROLLING ELEMENT FOR REGIOCHEMISTRY AND STEREOCHEMISTRY
MIKAMI, K
LOH, TP
NAKAI, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) : 6737 - 6738
[10] DIASTEREOCONTROL VIA LEWIS ACID-PROMOTED ENE REACTION WITH GLYOXYLATES AND ITS APPLICATION TO STEREOCONTROLLED SYNTHESIS OF A 22R-HYDROXY-23-CARBOXYLATE STEROID SIDE-CHAIN
MIKAMI, K
LOH, TP
NAKAI, T
[J]. TETRAHEDRON LETTERS, 1988, 29 (48) : 6305 - 6308

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