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

A plausible biosynthetic pathway for the isomeric marine alkaloids papuamine and haliclonadiamine via the double tandem ene cyclisation of a tetraenediimine is proposed. Initial model studies directed toward the biomimetic synthesis of these alkaloids are described which illustrate that the Lewis ac...

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Bibliographic Details
Published inTetrahedron Vol. 56; no. 4; pp. 623 - 628
Main Authors Adlington, RM, Baldwin, JE, Challis, GL, Cox, RJ, Pritchard, GJ
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 21.01.2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DESS-MARTIN PERIODINANE
SPONGE
dienes
ene reactions
steric and strain effects
CYCLOHEXANES
enals
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Summary:A plausible biosynthetic pathway for the isomeric marine alkaloids papuamine and haliclonadiamine via the double tandem ene cyclisation of a tetraenediimine is proposed. Initial model studies directed toward the biomimetic synthesis of these alkaloids are described which illustrate that the Lewis acid-promoted ene cyclisation of methyl-2-(methoxycarbonyl)dodeca-2,8-dienoate is critically dependent on the Delta-8 geometry. (C) 2000 Elsevier Science Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/S0040-4020(99)01011-X