5 単純キラル素子を用いた生物活性を有する天然物の合成
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Starting from simple chiral synthons, several biologically active natural products were synthesized. All four stereoisomers of 16-heptadecene-1,2,4-triol (1), an antimicrobial component of avocado fruit, were synthesized from a single starting material, (S)-2,2-dimethyl-1,3-dioxolane-4-ethanal, which was derived from L-malic acid. Natural triol was proved to have 2R, 4R configuration. 9,10-Epoxy-16-heptadecene-4,6-diyn-8-ol, a nematicidal constituent of Cirsium japonicum, was synthesized from 2,3-O-isopropylidene-D-glyceraldehyde. The absolute stereochemistry of natural epoxy-alcohol was determined to be 8R, 9R, 10S. Monilidiol (22) and dechloromonilidiol (23), phytotoxic metabolites of Monilinia fructicola , were synthesized from glyceraldehyde derivatives (12 and 46). The absolute configuration of their glycol part on the side chain was confirmed as 3'R, 4'S. A facile and efficient synthetic methods of 1,2: 5,6-di-O-cyclohexylidene-D-mannitol (44) and 2,3-O-cyclohexylidene-D-glyceraldehyde (46) were developed. Syntheses of pyriculariol, osmunda lactone derivative and phomalactone will be presented.
- 天然有機化合物討論会の論文
- 1985-09-07
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