Synthesis of cytotoxic cembranolide analogues via acid-induced opening of oxiranes

Authors
Rodriguez, AD Pina, IC Acosta, AL Barnes, CL
Citation
Ad. Rodriguez et al., Synthesis of cytotoxic cembranolide analogues via acid-induced opening of oxiranes, TETRAHEDRON, 57(1), 2001, pp. 93-107
Citations number
23
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
1
Year of publication
2001
Pages
93 - 107
Database
ISI
SICI code
0040-4020(20010101)57:1<93:SOCCAV>2.0.ZU;2-M
Abstract
A large series of analogues of Eunicea cembranolides 1-3 were synthesized w ith the purpose of evaluating their cytotoxicity against 60 human cancer ce ll-lines. Most of the analogues were as active as the lead compounds and a few displayed increased cytotoxicity. Their syntheses were based on the spe cific reactivity and stereochemistry of the epoxide substructure and involv ed highly regio- and diastereoselective acid-induced chemical transformatio ns. (C) 2000 Elsevier Science Ltd. All rights reserved.