Rapid construction of the aza-propellane core of acutumine via a photochemical [2 + 2] cycloaddition reaction.

作者: Raul Navarro , Sarah E. Reisman

DOI: 10.1021/OL3017963

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摘要: Synthetic efforts toward the chlorinated aza-propellane alkaloid acutumine (1) are described. The key vicinal quaternary centers were constructed by a photochemical [2 + 2] cycloaddition reaction of furanyl-tetrahydroindolone. Dihydroxylation product enabled tandem retro-aldol/intramolecular ketalization reaction, which revealed core 1 while generating an unusual, caged, pentacyclic hemiketal product.

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