43 生物活性を有する6-Substituted-5,6-dihydro-5-hydroxy(or acyloxy)-2H-pyran-2-one類の合成研究

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A series of biologically active 6-substituted-5,6-dihydro-5-hydroxy(or acyloxy)-2H-pyran-2-ones, (-)-osmundalactone(1) from Osmunda japonica(Akaboshi zenmai), (+)-phomalactone(2) from Nigrospore sp. and Phoma sp., (+)-acetylphomalactone(4) and (+)-asperlin(3) from Aspergillus sp. and their isomers were synthesized in optically active forms. 2,3-O-cyclohexylidene-D-glyceraldehyde(6) was converted to (S)-2-benzoyloxypropanal and (E),(S)-2-benzoyloxy-3-pentenal. The reaction between latter aldehyde and propargyl alcohol derivative gave, after several steps, the aforementioned dihydropyranones and their isomers. The signs of optical rotations of the dihydropyranones were largely dependent on the absolute configurations of C-4, that is, 5-(S)-dihydropyranones showed dextrorotatory, while 5-(R)-dihydropyranones were levorotatory. Biological activities of the newly synthesized compounds will be presented.
天然有機化合物討論会の論文
1986-09-09