Synthesis of chiral trans-syn-cis and trans-anti-trans [6.6.6] tricycles by transannular Diels-Alder reaction

Authors
Lavoie, R Toro, A Deslongchamps, P
Citation
R. Lavoie et al., Synthesis of chiral trans-syn-cis and trans-anti-trans [6.6.6] tricycles by transannular Diels-Alder reaction, TETRAHEDRON, 55(45), 1999, pp. 13037-13050
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
45
Year of publication
1999
Pages
13037 - 13050
Database
ISI
SICI code
0040-4020(19991105)55:45<13037:SOCTAT>2.0.ZU;2-1
Abstract
Stereocontrolled asymmetric synthesis and transannular Diels-Alder (TADA) r eaction of a 14-membered trans-cis-cis (TCC) macrocyclic trienone with an a ctivated dienophile leading to an A.B.C [6.6.6] tricycle having one angular methyl group is reported. The results of thermal and Lewis acid catalyzed TADA reaction are discussed. (C) 1999 Elsevier Science Ltd. All rights rese rved.