Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5232319 | Tetrahedron | 2006 | 6 Pages |
Abstract
The oxidative system MTO/30%H2O2/HBF4/fluorous alcohol is promising for the selective synthesis of biologically important antimalarial dispiro-1,2,4,5-tetraoxanes by direct acid-catalysed cyclisation of various 4-substituted cyclohexanones (1, R=Me, Et, tBu, Ph, COOEt, CF3). The role of the substitutent at the 4-position was important in the selectivity of formation of tetraoxane (2, TO) with respect to hexaoxonane (3, HO). By the use of fluorinated alcohols and under the right reaction conditions, tetraoxanes 2 were selectively formed and synthesised in 46-86% isolated yield from 4-substituted cyclohexanones 1.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Katja Žmitek, Stojan Stavber, Marko Zupan, Danièle Bonnet-Delpon, Jernej Iskra,