A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne:: a key intermediate for terbinafine

被引：4

作者：

Chou, SY ^{[1
]}

Tseng, CL ^{[1
]}

Chen, SF ^{[1
]}

机构：

[1] Dev Ctr Biotechnol, Taipei, Taiwan

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 20期

关键词：

halogenation; terbinafine; boron trichloride; trans olefin;

D O I：

10.1016/S0040-4039(00)00511-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study of the stereoselective halogenation of 6,6-dimethyl-1-hepten-4-yn-3-ol (1) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation (E:Z=9:1(max)). The resulting (E)-1-halo-6,6-dimethyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield and stereoselectivity. Two structurally related enyne alcohols have been studied likewise and shown similar versatility. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3895 / 3898

页数：4

共 9 条

[1]

Larock, 1989, COMPREHENSIVE ORGANI, P353

[2]

MARCH J, 1985, ADV ORG CHEM, P128

[3]

MEKI N, 1991, Patent No. 5021446

[4]

MEKI N, 1991, Patent No. 5036158