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Exploitation of Cyclopropane Carbaldehydes to Prins Cyclization: Quick Access to ( E)-Hexahydrooxonine and
Pankaj Kumar1, Raghunath Dey1, Prabal Banerjee1
1Department of Chemistry , Indian Institute of Technology Ropar , Nangal Road , Rupnagar , Punjab 140001 , India.
Abstract:
A single-step TiX4-mediated Prins-type cyclization of cyclopropane carbaldehydes with 3-buten-1-ol for the highly stereoselective construction of relatively strained ( E)-hexahydrooxonines is reported. Switching the alcohol to 3-butyn-1-ol prompted a similar route, augmented by another cyclization within a nine-membered ring to afford a bicyclized product (4,4-dihalo-5-aryloctahydrocyclopenta[ b]pyran). Easy transformation of the resulting geminal dihalide to a vinyl halide and a ketone further supplemented the substance of this approach.
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