Improved syntheses of methyl (14E)- and (14Z)-dehydrocrepenynate:: key intermediates in plant and fungal polyacetylene biosynthesis

被引：7

作者：

Zhu, L ^{[1
]}

Minto, RE ^{[1
]}

机构：

[1] Miami Univ, Dept Chem & Biochem, Oxford, OH 45056 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 23期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(01)00577-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient syntheses of the (14E)- and (14Z)-isomers of methyl dehydrocrepenynate have been achieved. The key steps involve Pd-catalyzed cross-coupling reactions furnishing the C:C double bonds: between C14 and C15, followed by Wittig reactions to construct the (Z)-alkene at C9. High overall yields and stereoselectivities were achieved for both isomers. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3803 / 3805

页数：3

相关论文

共 15 条

[1]

BARLEY GC, 1987, J CHEM RES-S, P232

[2] POLYACETYLENIC COMPOUNDS .219. BIOGENESIS OF C17-ENE-DIYNE-DIENES [J].

BOHLMANN, F ;

WEBER, D .

CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (09) :3020-3025

[3] NATURAL ACETYLENES .32. SYNTHESIS OF CREPENYNIC ACID - (OCTADEC-9-EN-12-YNOIC ACID) [J].

BRADSHAW, RW ;

DAY, AC ;

JONES, ERH ;

PAGE, CB ;

THALLER, V .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (06) :1156-&

[4] VINYLIC ORGANOBORANES .12. SYNTHESIS OF (Z)-1-HALO-1-ALKENES VIA HYDROBORATION OF 1-HALO-1-ALKYNES FOLLOWED BY PROTONOLYSIS [J].

BROWN, HC ;

BLUE, CD ;

NELSON, DJ ;

BHAT, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6064-6067

[5] ORIGIN OF NATURALLY-OCCURRING ACETYLENES [J].

BULOCK, JD ;

SMITH, GN .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (05) :332-&

[6] DIFFERENTIAL INHIBITION OF THROMBOXANE-B2 AND LEUKOTRIENE-B4 BIOSYNTHESIS BY 2 NATURALLY-OCCURRING ACETYLENIC FATTY-ACIDS [J].

CROFT, KD ;

BEILIN, LJ ;

FORD, GL .

BIOCHIMICA ET BIOPHYSICA ACTA, 1987, 921 (03) :621-624

[7]

FARRELL LW, 1987, J CHEM RES S, P234

[8] CREPENYNIC ACID AND MUSCLE BREAKDOWN [J].

FORD, GL ;

FOGERTY, AC ;

WALKER, KH .

PROGRESS IN LIPID RESEARCH, 1986, 25 :263-267

[9] AFZELIA CUANZENSIS SEED OIL - A SOURCE OF CREPENYNIC AND 14,15-DEHYDROCREPENYNIC ACID [J].

GUNSTONE, FD ;

KILCAST, D ;

POWELL, RG ;

TAYLOR, GM .

CHEMICAL COMMUNICATIONS, 1967, (06) :295-+

[10]

HEYWOOD VH, 1977, BIOL CHEM COMPOSITAE, V1, P284