A MILD AND EFFICIENT ROUTE TO THE PHARMACOPHORE OF THE ENEDIYNE ANTITUMOR AGENTS - (Z)-1,6-[BIS (TRIMETHYLSILYL)]-HEX-3-ENE-1,5-DIYNE VIA A NOVEL CARBENOID COUPLING REACTION

被引：29

作者：

HUBER, RS ^{[1
]}

JONES, GB ^{[1
]}

机构：

[1] CLEMSON UNIV,DEPT CHEM,CLEMSON,SC 29634

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(00)76998-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Z)-1,6-[Bis (trimethylsilyl)] -hex-3-ene-1,5-diyne has been prepared in high yield and in one pot from trimethylsilylpropargyl bromide by a remarkably stereoselective tandem carbenoid coupling-HX elimination sequence.

引用

页码：2655 / 2658

页数：4

共 7 条

[1]

BRANDSMA L, 1990, PREPARATIVE POLAR OR, V2

[2] TOTAL SYNTHESIS OF CALICHEAMICINONE - NEW ARRANGEMENTS FOR ACTUATION OF THE REDUCTIVE CYCLOAROMATIZATION OF AGLYCON CONGENERS [J].

HASELTINE, JN ;

CABAL, MP ;

MANTLO, NB ;

IWASAWA, N ;

YAMASHITA, DS ;

COLEMAN, RS ;

DANISHEFSKY, SJ ;

SCHULTE, GK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3850-3866

[3]

JONES GB, 1993, 45TH S E REG ACS M J

[4] CHEMISTRY AND BIOLOGY OF THE ENEDIYNE ANTICANCER ANTIBIOTICS [J].

NICOLAOU, KC ;

DAI, WM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (11) :1387-1416

[5] HALOMETHYL-METAL COMPOUNDS .72. PREPARATION OF ALPHA-HALOCYCLOPROPYL DERIVATIVES OF LITHIUM AND THEIR APPLICATION IN SYNTHESIS OF ALPHA-HALOCYCLOPROPYL COMPOUNDS OF SILICON, GERMANIUM, TIN, LEAD, AND MERCURY - NOVEL ISOMERIZATION OF SYN-7-BROMO-ANTI-7-LITHIONORCARANE TO ANTI-7-BROMO-SYN-7-LITHIO ISOMER [J].

SEYFERTH, D ;

LAMBERT, RL ;

MASSOL, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 88 (03) :255-286

[6] MONOHALOMETHYLLITHIUM XCH2LI - STABILIZATION OF A POTENTIAL SYNTHETIC REAGENT [J].

TARHOUNI, R ;

KIRSCHLEGER, B ;

RAMBAUD, M ;

VILLIERAS, J .

TETRAHEDRON LETTERS, 1984, 25 (08) :835-838

[7]

Vollhardt K.P.C., 1985, TETRAHEDRON LETT, V26, P709, DOI [10.1016/S0040-4039(00)89115-7, DOI 10.1016/S0040-4039(00)89115-7]

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