Total synthesis and assignment of the double-bond position and absolute configuration of (-)-pyrinodemin A.
[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.
Morimoto
Yoshiki
Y
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan. morimoto@sci.osaka-cu.ac.jp
Kitao
Satoru
S
Okita
Tatsuya
T
Shoji
Takamasa
T
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
D010080:Oxazoles; D011725:Pyridines; C430117:pyrinodemin A