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A facile domino strategy has been developed for the synthesis of a biologically active cyclopent-2-enone core containing combretastatin A-4 (CA-4) analogues from aryloxirane and aryl aldehyde. This one-pot method involves… Click to show full abstract
A facile domino strategy has been developed for the synthesis of a biologically active cyclopent-2-enone core containing combretastatin A-4 (CA-4) analogues from aryloxirane and aryl aldehyde. This one-pot method involves a sequence of semipinacol rearrangement, iterative aldol condensation, and iso-Nazarov cyclization reactions. The scope of this methodology is further shown in the enantioselective synthesis of 5-hydroxy-cyclopent-2-enones using the Sharpless AD catalyst. Biological studies reveal that (S)-enantiomers exhibit better inhibitory activity against cell proliferation than (R)-enantiomers.
Journal Title: Organic letters
Year Published: 2022
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