Practical Preparation of Bicyclohept-3-en-6-ones and its Utilisation in Stereoselective Total Synthesis of Grandisol and Lineatin via a Versatile Intermediate.

Article abstract of DOI:10.1016/S0040-4020(01)81119-4

New and efficient stereoselective total syntheses have been devised for racemic grandisol and lineatin, two important components of pheromonic blends.They are based on the utilisation of 1,4-dimethylbicyclo<3.2.0>hept-3-en-6-one as a pivotal intermediate.This compound, as well as other bicyclo<3.2.0>hept-3-en-6-ones, are now easily available by a practical bicyclization of the corresponding 3-hydroxy-6-alkenoic acids.