Concise Total Synthesis of (+)-Atlanticone C

SYNLETT(2020)

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摘要
The first enantioselective total synthesis of (+)-atlanticone C is described. The complex tricyclic protoilludane core was rapidly assembled by a photochemical reaction cascade starting from an easily accessible indanone precursor (3 steps). Optimization of an enantioselective Corey-Bakshi-Shibata reduction permitted a catalytic chiral reso-lution of the racemic photoproduct (45% over two steps; up to 98% ee). The enantiomerically enriched photoproduct was efficiently transformed into the (+)-enantiomer of atlanticone C (10 steps; 18% yield), and the absolute configuration of naturally occurring (-)-atlanticone C was thereby determined.
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关键词
asymmetric synthesis,total synthesis,photocycloaddition,chiral resolution,protoilludanes,atlanticone C
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