Domino Semipinacol/Iterative Aldol/Iso-Nazarov Cyclization to Triaryl-cyclopentenone: Enantioselective Synthesis of
Narra Rajashekar Reddy1, Shaik Gouse1, Sudhagar Selvaraju1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, Tamil Nadu, India.
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.
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