Total synthesis and assignment of the double-bond position and absolute configuration of (-)-pyrinodemin A |
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Authors: | Morimoto Yoshiki Kitao Satoru Okita Tatsuya Shoji Takamasa |
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Institution: | Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan. morimoto@sci.osaka-cu.ac.jp |
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Abstract: | structure: see text] The first asymmetric total synthesis of a structurally novel cis-cyclopentc]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. |
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