Diastereoselective synthesis of dihydropyrans via Prins cyclization of enol ethers: total asymmetric synthesis of (+)-civet cat compound.
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.
Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781039, India.
Sabera
S
Sultana
Kiran
K
Indukuri
Manash J
MJ
Deka
Anil K
AK
Saikia
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004987:Ethers / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D045949:Viverridae
D001688:Biological Products; D004987:Ethers; D011714:Pyrans