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Synthesis of alexine-like compounds from chiral five-membered endocyclic enecarbamates |
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| Authors: | Marcelo Siqueira Valle Carlos Roque Duarte Correia |
| Institution: | a Institute of Chemistry, State University of Campinas—UNICAMP, PO Box 6154, CEP 13084-971, Campinas-SP, Brazil b Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France |
| Abstract: | Stereoselective syntheses of enantiomerically enriched trihydroxy pyrrolizidine and indolizidines were accomplished from a common chiral endocyclic enecarbamate. The synthetic strategy features an efficient 2+2] cycloaddition of ketenes to the endocyclic enecarbamate and a highly regioselective Baeyer-Villiger oxidation of the intermediate azabicyclic-cyclobutanones. These new heterocycles are compounds structurally related to the alexines. |
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