Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H has been achieved. Key step involved construction of all-carbon quaternary carbon by palladium-catalyzed conjugate addition of arylboronic acid to 3-methyl cyclohexenone. Furthermore, a new approach to build [6-5-6] tricyclic backbone via formyl introduction and subsequent aldol-type condensation was also explored. (C) 2014 Elsevier Ltd. All rights reserved.
1.Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resources, Minist Educ, Kunming 650091, Peoples R China 2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China 3.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
Li,Liang-Qun;Li,Ming-Ming;Chen,Dong;Liu,Hao-Miao;Geng,Hui-Chun;Lin,Jun;Qin,Hong-Bo.Catalytic asymmetric formal total synthesis of (+)-dichroanone and (+)-taiwaniaquinone H,TETRAHEDRON LETTERS,2014,55(43):5960-5962