Chemistry - A European Journal p. 8701 - 8704 (2019)
Update date:2022-09-26
Topics:
Nakamura, Hugh
Kawakami, Manami
Tsukano, Chihiro
Takemoto, Yoshiji
A concise route for construction of the ACDE ring skeleton in calyciphylline A type alkaloids was developed using an intramolecular [5+2] cycloaddition reaction of an oxidopyrylium species bearing a tetrasubstituted olefin. Key to the success of this reaction was the combination of acid and base, which accelerated the construction of this skeleton containing a spiro ring and vicinal quaternary carbon centers. The resultant tricyclic ADE ring compound was converted to an ACDE ring model through C?H oxidation and an aza-Wittig reaction.
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