HIGHLY SELECTIVE SYNTHESIS OF VITAMIN-A AND ITS DERIVATIVES - CRITICAL COMPARISON OF SOME KNOWN PALLADIUM-CATALYZED ALKENYL-ALKENYL COUPLING REACTIONS

被引：65

作者：

NEGISHI, E

OWCZARCZYK, Z

机构：

[1] Department of Chemistry, Purdue University, West Lafayette

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(00)93574-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Vitamin A has been synthesized cleanly and selectively with essentially complete control of stereo- and regiochemistry in four linear and six overall steps from beta-ionone and (E)-3-methyl-2-penten-4-yn-1-ol via Pd-catalyzed cross coupling of an alkenylzinc with an alkenyl iodide; the use of other metals, such as Al, Zr, Mg, B, Cu, and Sn, being inferior to that of Zn.

引用

页码：6683 / 6686

页数：4

共 24 条

[21] STEREOCONTROLLED SYNTHESIS OF VITAMIN-A THROUGH A DOUBLE ELIMINATION-REACTION - A NOVEL CONVERGENT C10+C10 ROUTE
OTERA, J
MISAWA, H
ONISHI, T
SUZUKI, S
FUJITA, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) : 3834 - 3838
[22] PALLADIUM-CATALYZED COUPLING OF VINYL TRIFLATES WITH ORGANOSTANNANES - A SHORT SYNTHESIS OF PLERAPLYSILLIN-1
SCOTT, WJ
CRISP, GT
STILLE, JK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (16) : 4630 - 4632
[23] HIGHLY STEREOSELECTIVE SYNTHESIS OF VITAMIN-A AND ALL-TRANS RETINOIC ACID BY LOW-VALENT TITANIUM INDUCED REDUCTIVE ELIMINATION
SOLLADIE, G
GIRARDIN, A
[J]. TETRAHEDRON LETTERS, 1988, 29 (02) : 213 - 216
[24] ZWEIFEL G, 1970, J AM CHEM SOC, V92, P4086

← 1 2 3 →