Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 65, Issue 21, Pages 7110-7113Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo000816i
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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 trimethylsilyl-acetylene proceeded at room temperature in excellent yield.
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