A concise formal total synthesis of mappicine and nothapodytine B via an intramolecular hetero Diels-Alder reaction.
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.
Toyota
M
M
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai, 980-8578, Japan.
Komori
C
C
Ihara
M
M
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*
D000470:Alkaloids; D000998:Antiviral Agents; D007212:Indolizines; D011804:Quinolines; C008325:mappicine; C414097:nothapodytine B; D010165:Palladium