title: Enantioselective Total Synthesis of (-)-Alstoscholarisine A.
abstract: We report a concise and highly enantioselective total synthesis of (-)-alstoscholarisine A (1), a recently isolated monoterpenoid indole alkaloid that has significant bioactivity in promoting adult neuronal stem cells proliferation. A highly enantioselective (99% ee), intramolecular Ir-catalyzed Friedel-Crafts alkylation of indole 9 with a secondary allylic alcohol was utilized to establish the first stereogenic center upon which the other three contiguous chiral centers were readily set by a highly stereoselective tandem 1,4-addition and aldol reaction. The key tetrahydropyran was constructed through a hemiacetal reduction, and the final aminal bridge was forged by a one-pot reductive amination/cyclization. The conciseness of this approach was highlighted by building core bonds in each step with a minimalist protecting group strategy.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.|University of Chinese Academy of Sciences , Beijing 100049, China.
authors.forename: Xiao
authors.initials: X
authors.lastname: Liang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
authors.forename: Shi-Zhi
authors.initials: SZ
authors.lastname: Jiang
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
authors.forename: Kun
authors.initials: K
authors.lastname: Wei
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201, China.
authors.forename: Yu-Rong
authors.initials: YR
authors.lastname: Yang
mesh_terms: D046948:Secologanin Tryptamine Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D046948:Secologanin Tryptamine Alkaloids; C000608896:alstoscholarisine H