Bon, David J.-Y. DBanwell, MartinWillis, Anthony2015-12-100040-4020http://hdl.handle.net/1885/57495The first total synthesis of the hirsutene-type sesquiterpenoid natural product (+)-connatusin B (2) is reported. The cis-1,2-dihydrocatechol 3, which is obtained in enantiomerically pure form via the enzymatic dihydroxylation of toluene, served as the starting material. Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions represent key chemical steps in the reaction sequence leading to the cyclopropane ring-fused linear triquinane 14. Reductive cleavage of the three-membered ring within this framework and various functional group interconversions then provide the title compound 2.Keywords: connatusin b; hirsutene; sesquiterpene derivative; unclassified drug; article; chemical reaction; cycloaddition; Diels Alder reaction; dihydroxylation; drug structure; drug synthesis; enantiomer; priority journal; Alnus Chemoenzymatic; Connatusin B; Diels-Alder; Oxa-di-p-methane; Photochemistry; Sesquiterpene201010.1016/j.tet.2010.07.0592016-02-24