title: Extending Pummerer reaction chemistry: studies in the palau'amine synthesis area.
abstract: Exploratory oxidative cyclization studies on cyclopentanelated and cyclohexenelated oroidin derivatives utilized Pummerer chemistry to generate pentacyclic structures related to the palau'amine family of sponge metabolites. Stereochemical issues were paramount, and appropriate choice of annelated ring size led to formation of the pentacyclic framework with complete diastereoselectivity for all of the core bonds.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. ksf@chem.psu.edu
authors.forename: Ken S
authors.initials: KS
authors.lastname: Feldman
authors.forename: Ahmed Yimam
authors.initials: AY
authors.lastname: Nuriye
authors.forename: Jianfeng
authors.initials: J
authors.lastname: Li
mesh_terms: D000588:Amines / Q000138:chemical synthesis*; D003500:Cyclization; D019281:Dimerization; D006571:Heterocyclic Compounds; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000588:Amines; D006571:Heterocyclic Compounds