Abstract
Nimbolide [systematic name: (4alpha,5alpha,6alpha,7alpha,15beta,17alpha)-7,15:21,23-diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-18,24-dinor-11,12-secochola-2,13,20,22-tetraene-4,11-dicarboxylic acid gamma-lactone methyl ester], C27H30O7, was isolated from the leaves of Azadirachta indica, and its isomer, isonimbolide [systematic name: (4alpha,5alpha,6alpha,7alpha,15alpha)-7,15:21,23-diepoxy-6-hydroxy-4,8-dimethyl-1-oxo-18,24-dinor-11,12-secochola-2,16,20,22-tetraene-4,11-dicarboxylic acid gamma-lactone methyl ester], was prepared from a novel rearrangement reaction of nimbolide, using boron trifluoride etherate and tetrabutylammonium bromide. The reaction conditions are probably responsible for the ether cleavage, double-bond rearrangement and reformation of the ether linkage. As a result, there are conformational changes in two cyclopentane rings and the side-chain -CH2COOMe group. In isonimbolide, an R(4)(4)(24) hydrogen-bond motif is observed.
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