A practical approach to enantiomerically pure cis-epoxides. Synthesis of (+)-disparlure

被引：21

作者：

SinhaBagchi, A

Sinha, SC

Keinan, E

机构：

[1] SCRIPPS RES INST, DEPT MOLEC BIOL, LA JOLLA, CA 92037 USA

[2] TECHNION ISRAEL INST TECHNOL, DEPT CHEM, IL-32000 HAIFA, ISRAEL

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 12期

关键词：

D O I：

10.1016/0957-4166(95)00405-X

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An efficient synthesis of (+)-disparlure has been achieved in >99.8% ee via the Sharpless asymmetric dihydroxylation followed by Mitsunobu inversion of one hydroxyl group and conversion of the resultant erythro diol to the cis epoxide.

引用

页码：2889 / 2892

页数：4

共 24 条

[1]

ACHMATOWICZ O, 1985, POL J CHEM, V59, P553

[2] POTENT SEX ATTRACTANT OF GYPSY MOTH - ITS ISOLATION, IDENTIFICATION, AND SYNTHESIS [J].

BIERL, BA ;

BEROZA, M ;

COLLIER, CW .

SCIENCE, 1970, 170 (3953) :87-+

[3] SYNTHESIS AND ACTIVITY OF OPTICALLY-ACTIVE DISPARLURE [J].

IWAKI, S ;

MARUMO, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (25) :7842-7844

[4] AN ENANTIOSPECIFIC SYNTHESIS OF (+)-DISPARLURE FROM CARBOHYDRATE PRECURSORS [J].

JIGAJINNI, VB ;

WIGHTMAN, RH .

CARBOHYDRATE RESEARCH, 1986, 147 (01) :145-148

[5] SYNTHESIS OF ALL 4 ISOMERS OF DISPARLURE USING OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION [J].

KEINAN, E ;

SINHA, SC ;

SINHABAGCHI, A ;

WANG, ZM ;

ZHANG, XL ;

SHARPLESS, KB .

TETRAHEDRON LETTERS, 1992, 33 (43) :6411-6414

[6] CIS-EPOXIDES VIA SHARPLESS ASYMMETRIC DIHYDROXYLATION REACTION SYNTHESIS OF (+)-DISPARLURE [J].

KO, SY .

TETRAHEDRON LETTERS, 1994, 35 (21) :3601-3604

[7] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[8] A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].

KOLB, HC ;

SHARPLESS, KB .

TETRAHEDRON, 1992, 48 (48) :10515-10530

[9]

LIN GQ, 1985, ACTA CHIM SINICA, P257

[10]

LIN GQ, 1984, ACTA CHIM SINICA, P74

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