Synthesis of Carbocycles via Intramolecular Conjugate Additions: Another Solution to the Terpenoid Side Chain Stereochemistry Problem.
Intramolecular conjugate additions of keto esters 7-11, mediated by pyrrolidine-acetic acid, provide perhydroindans or bicyclo[6.3.0]undecanes with high levels of diastereoselectivity at the acyclic stereogenic center. Levels of acyclic diastereoselection depend on starting unsaturated ester olefin geometry.
Guevel
Alyx-Caroline
AC
Department of Chemistry, The Ohio State University, 120 W. 18th Avenue, Columbus, Ohio 43210.
Hart
David J.
DJ