Synthetis studies on biologically active unsaturated lactones of microbial origin.
| Project/Area Number |
60560125
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
製造化学・食品
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| Research Institution | TOHOKU UNIVERSITY |
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Principal Investigator |
YAMASHITA Kyohei Professor, Faculty of Agriculture, Tohoku University, 農学部, 教授 (90005570)
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| Co-Investigator(Kenkyū-buntansha) |
SUGIYAMA Takeyoshi Research Associate, Faculty of Agriculture, Tohoku University, 農学部, 助手 (10125586)
TANAKA Akira Research Associate, Faculty of Agriculture, Tohoku University, 農学部, 助手 (70005651)
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| Project Period (FY) |
1985 – 1986
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| Project Status |
Completed (Fiscal Year 1986)
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| Budget Amount *help |
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1986: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1985: ¥1,500,000 (Direct Cost: ¥1,500,000)
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| Keywords | Organic synthesis / Biologically active substances / Unsaturated lactones / Microbial metabolites / Pyrenolide B / Osmundalactone / Phomalactone / Asperlin |
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| Research Abstract |
1. Syntheses of pyrenolides: Pyrenolides are a series of biologically active decanolides produced by Pyrenophora teres. We synthesized pyrenolide B from 2-methylcyclononanone via decan-9-olide (phoracantholide) and established a new synthetic route to decanolide skeleton.
2. Syntheses of asperlin and related natural products.
(1) Synthesis of (-)-osmundalactone: there are many biologically active 6-substituted 5,6-dihydro-5-hydroxy (or acyloxy)-2H-pyran-2-ones in nature. To establish a synthetic route to optically active pyranones, (-)-osmundalactone, the simplest natural analog, was synthesized from 3-triethylsiloxy-1-propyne and (S)-1-methyl-2-oxoethyl benzoate, which was derived from 2,3-O-cyclohexylidene-D-glyceraldehyde.
(2) Syntheses of natural (+)-phomalactone and its isomers : Phomalactone, isolated from Nigerospora sp., was firstly synthesized by a similar strategy as above. (E,S)-2-Benzoyloxy-3-pentenal was reacted with 1-lithoi-3-triethyl-siloxy-1-propynr. After several steps including protection, deprotection, partial hydrogenation, oxidative lactonization and deprotection, (+)-phomalactone and its diastereomer were obtained.
(3) Synthesis of (+)-asperlin and its isomer : Acetylation of (+)-phomalactone followed by oxidation afforded (+)-asperlin and (1'R,2'S)-isomer.
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Report
(1 results)
Research Products
(6 results)
