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Diastereoselective Synthesis of Dihydropyrans via Prins Cyclization of Enol Ethers: Total Asymmetric Synthesis of (+)-Civet Cat Compound

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journal contribution
posted on 06.12.2013, 00:00 by Sabera Sultana, Kiran Indukuri, Manash J. Deka, Anil K. Saikia
Trimethylsilyl trifluoromethanesulfonate (TMSOTf) can be efficiently used for Prins cyclization of acrylyl enol ethers to 5,6-dihydro-2H-pyran-2-acetates stereo- and regioselectively in good yields. The methodology was used for the total synthesis of natural product (+)-civet.