March 3, 2026Open Access

Synthesis of some cis-4,4-dimethyl-2-isopropenylcyclopentane derivatives as potential intermediates towards the protoilludane skeleton

Key Points

The synthesis predominantly produces cis isomers of the cyclopentane derivatives, indicating a successful reaction pathway.
Three new compounds were synthesized using a thermally induced ene reaction as a pivotal step for their formation.
These compounds include dimethyl-substituted derivatives with potential applications in synthetic chemistry for sesquiterpenes.
The findings may enable further exploration of terpenoid structures, particularly those related to the protoilludane skeleton.

Abstract

The three gem-dimethyl-substituted cyclopentane derivatives 1-(2-propionyl)-4,4-dimethyl-2-isopropenylcyclopentane, 2-isopropenyl-4,4-dimethylcyclopentanecarboxyaldehyde and 1-hydroxy- methyl-2-isopropenyl-4,4-dimethylcyclopentane have been synthesized employing a thermally induced ene reaction as a key step. Each of the three compounds has been obtained predominantly as the cis isomer. The successful synthesis of these compounds affords opportunities for their further ellaboration towards sesquiterpenes of the protoilludane skeleton.

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Synthesis of some cis-4,4-dimethyl-2-isopropenylcyclopentane derivatives as potential intermediates towards the protoilludane skeleton

Key Points

Abstract

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