Studies Directed Towards the Synthesis of a Naturally Occurring Sesquiterpene, 4-Deoxy-10-Oxodihydrobotrydial by a Ti(III)-Mediated Radical Cyclization

Abstract

The Cp2TiCl-mediated opening of epoxides in α,β-unsaturated ester-appended substrates leads to a cascading 5-exo-trig radical cyclization followed by lactonization yielding bicyclic lactone rings. Leveraging this strategic approach has become crucial in the construction of the core structure of many sesquiterpenoid natural products. In our present study, we have synthesized the 1,8-di-epi isomer of 4-deoxy-10-oxodihydrobotrydial, a naturally occurring botryane employing the titanocene(III) radical cyclization strategy to build its [6,5,6]-fused tricyclic framework.