A short synthesis of (+/-)-laurene: mechanistic reinvestigation in palladium-catalyzed cycloreductions of 1,6-enynes

Authors
Oh, CH Han, JW Kim, JS Um, SY Jung, HH Jang, WH Won, HS
Citation
Ch. Oh et al., A short synthesis of (+/-)-laurene: mechanistic reinvestigation in palladium-catalyzed cycloreductions of 1,6-enynes, TETRAHEDR L, 41(43), 2000, pp. 8365-8369
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
43
Year of publication
2000
Pages
8365 - 8369
Database
ISI
SICI code
0040-4039(20001021)41:43<8365:ASSO(M>2.0.ZU;2-J
Abstract
Two palladium-catalyzed cycloreduction strategies have been applied for the synthesis of laurene. Palladium-catalyzed cyclizations of 1,6-enynes initi ally form the corresponding alkylpalladium intermediates. While triethylsil ane could directly reduce the intermediates to lead to the corresponding cy cloreduced products, the intermediates in the presence of even excess formi c acid underwent beta -elimination to yield the dienes that were further re duced at the less hindered olefins to yield the cycloreduced products. (C) 2000 Elsevier Science Ltd. All rights reserved.