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Nazarov Cyclization of Geminal-Benzoyl-Phenyl Allenes in Triflic Acid: A Synthetic Route to Pallidol-like Structures
Oussama Abdelhamid Mammeri1, Irina A Boyarskaya1, Dar'ya V Spiridonova1
1Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg 199034, Russia.
Abstract:
Benzoyl substituted allenes in Brønsted superacid TfOH at room temperature afford Nazarov cyclization products, E-/Z-alkylidene indanones. In TfOH at a higher temperature of 70 °C, allenes bearing geminal benzoyl and phenyl substituents undergo further transformations, yielding fused indano-indanones. The latter have been used as precursors in the stereoselective synthesis of the structural analogue of the natural compound, Pallidol.
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