title: Enantioselective Total Synthesis of (+)-Hinckdentine A via a Catalytic Dearomatization Approach.
abstract: Optically pure hinckdentine A was synthesized on a 300 mg scale via an asymmetric catalysis-based strategy. The key steps to the first asymmetric synthesis involved (i) enantioselective dearomative cyclization of an achiral N-acyl indole that allowed for the efficient construction of the key polycyclic indoline intermediate with a crucial tetrasubstituted stereogenic carbon center, (ii) Beckmann fragmentation-mediated ring expansion, (iii) rearrangement-based introduction of an anilinic nitrogen atom, (iv) regioselective tribromination, and (v) final closure of the cyclic amidine moiety.
authors: Graduate School of Pharmaceutical Sciences, Nagoya University , Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
authors: Kazuya
authors: K
authors: Douki
authors: Graduate School of Pharmaceutical Sciences, University of Tokyo , 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors: Hiroyuki
authors: H
authors: Ono
authors: Faculty of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University , Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors: Tohru
authors: T
authors: Taniguchi
authors: Graduate School of Pharmaceutical Sciences, Nagoya University , Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
authors: Jun
authors: J
authors: Shimokawa
authors: Graduate School of Pharmaceutical Sciences, Nagoya University , Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
authors: Masato
authors: M
authors: Kitamura
authors: Graduate School of Pharmaceutical Sciences, Nagoya University , Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.
authors: Tohru
authors: T
authors: Fukuyama
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007769:Lactams / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011799:Quinazolines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007769:Lactams; D011799:Quinazolines; C485801:hinckdentine A; D010165:Palladium