title: A concise formal total synthesis of mappicine and nothapodytine B via an intramolecular hetero Diels-Alder reaction.
abstract: A six-step formal total synthesis of a natural alkaloid, mappicine (3), has been achieved. The highlight of our synthetic strategy is an intramolecular hetero Diels-Alder reaction that was used for the construction of the CD ring system of mappicine (3). In addition, it was demonstrated that the Sonogashira coupling reaction of 2-chloro-3-hydroxymethylquinoline (8c) with trimethylsilylacetylene proceeded at room temperature in excellent yield.
authors.affiliation: Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai, 980-8578, Japan.
authors.forename: M
authors.initials: M
authors.lastname: Toyota
authors.forename: C
authors.initials: C
authors.lastname: Komori
authors.forename: M
authors.initials: M
authors.lastname: Ihara
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002384:Catalysis; D007212:Indolizines / Q000138:chemical synthesis*; D010165:Palladium; D011804:Quinolines / Q000138:chemical synthesis*
chemical_list: D000470:Alkaloids; D000998:Antiviral Agents; D007212:Indolizines; D011804:Quinolines; C008325:mappicine; C414097:nothapodytine B; D010165:Palladium