A Photochemical Approach to a Potential Precursor of the Bicyclo [6.4.0] Dodecane Ring System of Taxane Diterpenes

Abstract

The intermolecular [2+2] photocycloaddition of dimedone 6 and 1-acetoxy-2-methyl-5-dioxolan-1-hexene 7 followed by alkaline treatment, gave the 1,5,5,11-tetramethyl-7-dioxolan bicyclo [4,3,2]-4-decen-2,3-dione 12, and the 1,5,5-trimethyl-3-hydroxy-7-dioxolan bicyclo [5,4,1] dodecan-2,11-dione 13.

Key Words:

• Taxane
• [2+2] Photocycloaddition
• Dimedone
• Cyclobutane r ring opening
• De Mayo reaction
• Cyclization