Forming Spirocyclohexadienone-Oxocarbenium Cation Species in the Biomimetic Synthesis of Amomols

The oxidation of appropriate 2-(4-hydroxyphenyl)ethyl ketones gives direct access to amomols by means of the formation of a transient spirocyclohexadienone-oxocarbenium ion that is intermolecularly intercepted by an alcohol. Furthermore, homochiral amomols and other new analogues were synthesized fo...

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Bibliographic Details
Published in:Journal of organic chemistry 2011-03, Vol.76 (5), p.1409-1417
Main Authors: Traoré, Mariam, Maynadier, Marjorie, Souard, Florence, Choisnard, Luc, Vial, Henri, Wong, Yung-Sing
Format: Article
Language:English
Subjects:
Biomimetics
Cations - chemistry
Cations - metabolism
Chemistry
Cyclohexanes - chemistry
Cyclohexanes - metabolism
Exact sciences and technology
Furans - chemical synthesis
Furans - chemistry
Furans - metabolism
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Ketones - chemistry
Ketones - metabolism
Molecular Structure
Organic chemistry
Oxidation-Reduction
Plasmodium falciparum - chemistry
Plasmodium falciparum - metabolism
Preparations and properties
Spiro Compounds - chemistry
Spiro Compounds - metabolism
Stereoisomerism
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Summary:The oxidation of appropriate 2-(4-hydroxyphenyl)ethyl ketones gives direct access to amomols by means of the formation of a transient spirocyclohexadienone-oxocarbenium ion that is intermolecularly intercepted by an alcohol. Furthermore, homochiral amomols and other new analogues were synthesized for the first time and were biologically evaluated on Plasmodium falciparum.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo102414s