title: Total synthesis and assignment of the double-bond position and absolute configuration of (-)-pyrinodemin A.
abstract: [structure: see text] The first asymmetric total synthesis of a structurally novel cis-cyclopent[c]isoxazolidine alkaloid, (-)-pyrinodemin A (3), which exhibits potent cytotoxicity, has been accomplished through a highly diastereoselective intramolecular nitrone-olefin cycloaddition reaction as the key step. Thus, it has been found that the hitherto unknown absolute configuration of pyrinodemin A is as indicated in the structural formula 3.
authors.affiliation: Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan. morimoto@sci.osaka-cu.ac.jp
authors.forename: Yoshiki
authors.initials: Y
authors.lastname: Morimoto
authors.forename: Satoru
authors.initials: S
authors.lastname: Kitao
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Okita
authors.forename: Takamasa
authors.initials: T
authors.lastname: Shoji
mesh_terms: D000818:Animals; D003500:Cyclization; D008958:Models, Molecular; D008968:Molecular Conformation; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010080:Oxazoles; D011725:Pyridines; C430117:pyrinodemin A