Synthetic Approaches to Taxodione. Synthesis of Methyl 12-Oxopodocarpa-5,9(11)-diene-8β-Carboxylate

Abstract

In connection with studies leading to the total synthesis of taxodione¹ (1), we required the tricyclic enone 3. We have previously described² an AB→ABC approach to this intermediate which was flawed by a low yield in the penultimate closure of the C ring (2→3). We now wish to report an alternate synthesis of 3 which involves a BC→ABC approach for the construction of this tricyclic system.