Hydroalumination of 3-butyn-1-ol: Application to a stereoselective synthesis of (3E,5Z)-3,5-dodecadienyl acetate, the sex pheromone of the leaf roller moth

Authors
Chong, JM Heuft, MA
Citation
Jm. Chong et Ma. Heuft, Hydroalumination of 3-butyn-1-ol: Application to a stereoselective synthesis of (3E,5Z)-3,5-dodecadienyl acetate, the sex pheromone of the leaf roller moth, TETRAHEDRON, 55(50), 1999, pp. 14243-14250
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
50
Year of publication
1999
Pages
14243 - 14250
Database
ISI
SICI code
0040-4020(199912)55:50<14243:HO3ATA>2.0.ZU;2-7
Abstract
Hydroalumination-iodinolysis of 3-butyn-1-ol (2) provided E-4-iodo-3-buten- 1-ol (4E) as the major product. This compound was transformed in three step s into the leaf roller moth sex pheromone 1 with high (>99% de) stereoselec tivity and good overall yield (4 steps, 39% from 2). (C) 1999 Elsevier Scie nce Ltd. All rights reserved.