title: Total synthesis of indole alkaloid alsmaphorazine D.
abstract: A concise total synthesis of rac-alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the δ-lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo[2,3-b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo[3.3.1]nonane structure; and 4) a one-pot desilylation/double epimerization reaction that affirms the relative stereochemistry.
authors.affiliation: Department of Chemistry, Zhejiang University, 148 Tianmushan Road, Hangzhou 310028 (China).
authors.forename: Chenlong
authors.initials: C
authors.lastname: Zhu
authors.forename: Zhaobo
authors.initials: Z
authors.lastname: Liu
authors.forename: Guanyu
authors.initials: G
authors.lastname: Chen
authors.forename: Kai
authors.initials: K
authors.lastname: Zhang
authors.forename: Hanfeng
authors.initials: H
authors.lastname: Ding
mesh_terms: D031051:Alstonia / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D002563:Cerium / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D018515:Plant Leaves / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids; D002563:Cerium
keywords: cyclization; epimerization; oxidative coupling; pyrroloindoles; total synthesis