title: Stereoselective synthesis of the eastern quinolizidine portion of himeradine A.
abstract: The synthesis of the C(15)-C(17)/N(1')-C(11') quinolizidine portion of himeradine A is disclosed. An intramolecular, heteroatom Michael addition was employed to establish the C(6') stereogenic center with high diastereoselectivity. The quinolizidine ring was constructed using microwave-induced cyclization at the N(1')-C(2') position. The C(17) stereogenic center was introduced through a diastereoselective Overman rearrangement.
authors: Department of Chemistry, Oregon State University, Corvallis, Oregon 97331, USA.
authors: Nathan D
authors: ND
authors: Collett
authors: Rich G
authors: RG
authors: Carter
mesh_terms: D003500:Cyclization; D015394:Molecular Structure; D054837:Quinolizidines / Q000138:chemical synthesis*; D011807:Quinolizines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D054837:Quinolizidines; D011807:Quinolizines; C480481:himeradine A