Abstract
The first synthesis of racemic isoptychanolide (2) , a stereoisomer of natural ptychanolide (1) , which differs in the configuration of the oxirane function, is reported. The key steps were an α-alkinone cyclisation ( 5 → 4 gas phase flow thermolysis at 620°), a stereoselective exo allylation of the enolate ( F ) derived upon desoxygenation and reduction of the enol ether 10 , and elaboration of the two substituents at C (3) of the resulting 11 to afford the enol lactone 3 . Epoxidation of the double bond of 3 took place from the side of C(2) (and not of C(4)), so that isoptychanolide ( 2 ) was formed. The configurations of all stereocentres in 2 were determined by an X-ray analysis.
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