Abstract
Oxidative rearrangement of odollactone has been carried out with hydrogen peroxide containing p-toluene sulphonic acid in dichloromethane. The products obtained were characterised by chemical transformation using selenium dioxide in acetic acid, sodium dichromate in acetic acid and Li in ethylenediamine followed by spectral analysis. The in- troduction of olefinic double bond at AB-ring juncture influences the cleavage of γ-lactone ring to the diol in contrast to the parent odollactone that gives the carboxylic acid.
Highlights
Structure (1) for odollactone[1,2] has been characterized[3,4,5,6] from our laboratory from the plant Gynocardia Odorata available in the hill area of Darjeeling, detailed investigation in respect of its chemical activity has not yet been attempted so far
Keeping this view in mind and to explore the chemical activity of this naturally occurring 3β-hydroxy lactone of friedelane skeletone, we have studied some oxidative and reductive transformations on it
It has been reported[7] that friedelanol when heated with p-toluene sulfonic acid, undergoes rearrangement of the friedelane skeleton to oleanane skeleton via Wagner rearrangement[8]
Summary
Structure (1) for odollactone[1,2] has been characterized[3,4,5,6] from our laboratory from the plant Gynocardia Odorata available in the hill area of Darjeeling, detailed investigation in respect of its chemical activity has not yet been attempted so far. Keeping this view in mind and to explore the chemical activity of this naturally occurring 3β-hydroxy lactone of friedelane skeletone, we have studied some oxidative and reductive transformations on it. During the investigation some interesting observations were noted which comprise the subject matter of this report
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