Organic letters

Total synthesis and assignment of the double-bond position and absolute configuration of (-)-pyrinodemin A

Y Morimoto, S Kitao, T Okita, T Shoji

Index: Morimoto, Yoshiki; Kitao, Satoru; Okita, Tatsuya; Shoji, Takamasa Organic Letters, 2003 , vol. 5, # 15 p. 2611 - 2614

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Citation Number: 18

Abstract

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.