Aromatics to triquinanes: Studies on synthesis and photo reaction of endo-tricyclo [5.2.2.02,6] undecanes.

Abstract

Synthesis of endo-tricyclo[5.2.2.02.6]undecanes having a /3, y.enone chromophore and their photochemical reaction upon triplet excitation is described. The key reaction for the synthesis of tricycloundecanes (9-13) involves generation and interception of spiroepoxycyclohexa-2,4-dienone (5) with cyclopentadiene and transformation on the resulting adduct (6). Photoreaction of 11 gave a mixture of products due to 1,2-acyl shift and 7?-' + 7?-' cycloaddition. Irradiation of the hydroxyketone (10) furnished the triquinane (17) selectively, which was oxidized to give the embellished tri- quinane (15).research such as high-value fine chemicals, advanced starting products for semi-synthesis, plant-based industrial feedstock chemicals, chemical ecology, bioremediation, etc. So far only limited number of flora and organisms have been subjected to some kind of chemical or biological examination; thus vast majority of natural wealth remains unexplored. Studies on marine natural products initiated only recently have yielded molecules with exotic molecular architecture and diverse bioactivity. Well-directed research on natural products will enrich our bioresource base. In the current millennium, India is in a pre-eminent position to contribute towards natural product research with the utilization of its rich knowledge base and biodiversity.