title: Enantioselective synthesis of the R-enantiomer of the feeding deterrent (S)-ypaoamide.
abstract: The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment, and a lipase (CCL)-promoted deacetylation reaction to reach the orthogonal deprotection. Through this work the absolute configuration of the natural ypaoamide was determined as S.
authors.affiliation: Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, People's Republic of China.
authors.forename: Jie
authors.initials: J
authors.lastname: Chen
authors.forename: Pei-Qiang
authors.initials: PQ
authors.lastname: Huang
authors.forename: Yves
authors.initials: Y
authors.lastname: Queneau
mesh_terms: D001685:Biological Factors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001685:Biological Factors; D011759:Pyrrolidines; C545381:ypaoamide