Studies on the synthetic utility of [6+3]cycloaddition of pentafulvenes with 3-oxidopyrylium betaines: efficient synthesis of fused ring cyclooctanoids

Abstract

A study on the synthetic utility of [6+3] cycloaddition of pentafulvenes with 3-oxidopyrylium betaines is described. 5-8 Fused oxa-bridged cyclooctanoids, the products of the above methodology undergo facile Diels-Alder reaction, dipolar cycloaddition, Luche reduction and selective hydrogenation over Pd/C leading to functionalized molecules, which can be transformed to oxa-bridged fused cyclooctanoids. We have shown that the carbon framework of the molecules can be directly expanded from the product, thus enhancing the synthetic versatility of the products.