84(P-41) 微生物代謝産物(-)-neuchromenin,(-)-nocardione A及び(-)-nocardione Bの合成による絶対立体配置決定(ポスター発表の部)

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In 1996 (-)-neuchromenin (1) was isolated from the culture broth of Eupenicillium javanicum var. meloforme PF1181 as an inducer of neurite outgrowth of PC12 cells at concentration of 2.5-10 μg/ml. Its structure was deduced as 1 by extensive spectral analysis, although its absolute configuration remained unknown. In order to settle that stereochemical problem, we undertook the synthesis of both the enantiomers of neuchromenin using both the enantiomers of known aldehyde (11). By synthesizing both (R) and (S) enantiomers of neuchromenin, we found (S) enantiomer to be identical with the naturally occurring (-)-neuchromenin. In 2000 two new furano-o-naphthoquinones, (-)-nocardione B (2) and (-)-nocardione A (3) were isolated as new tyrosine phosphatase inhibitors with moderate antifungal and cytotoxic activities. Due to the scarcity of the materials, their absolute configuration remained unknown. In order to solve this problem, we undertook a synthesis of optically active nocardiones with known absolute configuration. (R)-(+)-Nocardione B (2) and (S)-(-)-nocardione A (3) were synthesized by starting from the commercially available enantiomers of propylene oxide and 5-benzyloxy (or methoxy)-1-tetralone. As a result, the absolute configuration of the naturally occurring (-)-nocardione A and (-)-nocardione B was established as S.
天然有機化合物討論会の論文
2001-09-01