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

Authors
Chou, SY Tseng, CL Chen, SF
Citation
Sy. Chou et al., A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: a key intermediate for terbinafine, TETRAHEDR L, 41(20), 2000, pp. 3895-3898
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
20
Year of publication
2000
Pages
3895 - 3898
Database
ISI
SICI code
0040-4039(20000521)41:20<3895:ASSO(A>2.0.ZU;2-G
Abstract
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 age nts investigated, boron trichloride is the most successful reagent for ster eoselective halogenation (E:Z=9:1(max)). The resulting (E)-1-halo-6,6-dimet hyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal a gent, is obtained in good yield and stereoselectivity. Two structurally rel ated enyne alcohols have been studied likewise and shown similar versatilit y. (C) 2000 Elsevier Science Ltd. All rights reserved.