Towards a biomimetic synthesis of the marine alkaloids papuamine and haliclonadiamine: Model studies

Authors
Adlington, RM Baldwin, JE Challis, GL Cox, RJ Pritchard, GJ
Citation
Rm. Adlington et al., Towards a biomimetic synthesis of the marine alkaloids papuamine and haliclonadiamine: Model studies, TETRAHEDRON, 56(4), 2000, pp. 623-628
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
4
Year of publication
2000
Pages
623 - 628
Database
ISI
SICI code
0040-4020(20000121)56:4<623:TABSOT>2.0.ZU;2-O
Abstract
A plausible biosynthetic pathway for the isomeric marine alkaloids papuamin e and haliclonadiamine via the double tandem ene cyclisation of a tetraened iimine is proposed. Initial model studies directed toward the biomimetic sy nthesis of these alkaloids are described which illustrate that the Lewis ac id-promoted ene cyclisation of methyl-2-(methoxycarbonyl)dodeca-2,8-dienoat e is critically dependent on the Delta-8 geometry. (C) 2000 Elsevier Scienc e Ltd. All rights reserved.