title: Total syntheses of anominine and tubingensin A.
abstract: A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6π-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
authors.forename: Ming
authors.initials: M
authors.lastname: Bian
authors.forename: Zhen
authors.initials: Z
authors.lastname: Wang
authors.forename: Xiaochun
authors.initials: X
authors.lastname: Xiong
authors.forename: Yu
authors.initials: Y
authors.lastname: Sun
authors.forename: Carlo
authors.initials: C
authors.lastname: Matera
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: Ang
authors.initials: A
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D000475:Alkenes; D001688:Biological Products; D002227:Carbazoles; D007211:Indoles; C550942:anominine