Total Synthesis of (+)-Komaroviquinone

+)-Komaroviquinone (1) was synthesized from enone 8 in twelve steps.Three novel routes were developed to produce key intermediate dienone 11.Two additional noteworthy steps are a regiospecific bromohydrin formation to oxidize C(7) and a second regio-and stereospecific bromohydrin formation to introduce the β-C(10) alcohol.During a systematic study of the organic extracts of the semishrub Dracocephalum komarovi Lipsky, 1 which grows between 2300-3600 meters above sea level in mountains of western Uzbekistan, Honda and co-workers isolated komaroviquinone (1)2 and coulterone (2). 2,3These compounds exhibit trypanocidal activity against the causative agent of Chagas' disease in Central and South America. 4The preceding manuscript detailed our synthesis of (±)-1 5 (Scheme 1) featuring a cyclialkylation strategy 6 to construct 7 Scheme 1 O 8 O CH 3 O OCH 3 OCH 3 OEt (±)-6 H AcO H H AcO