Systematic Synthesis of Terrestrial and Marine Terpenoid Dialdehydes
| Project/Area Number |
59470021
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
天然物有機化学
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| Research Institution | Osaka City University |
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Principal Investigator |
ISOE Sachihiko Faculty of Science, Osaka City University, 理学部, 教授 (90046946)
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| Project Period (FY) |
1984 – 1986
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| Project Status |
Completed (Fiscal Year 1986)
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| Budget Amount *help |
¥7,300,000 (Direct Cost: ¥7,300,000)
Fiscal Year 1986: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1985: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1984: ¥5,100,000 (Direct Cost: ¥5,100,000)
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| Keywords | Manoalide / Seco-manoalide / Neomanoalide / Secologanin / Penstemide / Didrovaltrate / Allamadicin / ブレフェルジンA |
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| Research Abstract |
1. The first synthesis of manoalide and seco-manoalide from methyl 7,8-dihydro- <beta> -ionylidene acetate was achieved in high yield by the new method utilizing regiospecific singlet oxygen oxidation of 3-alkeny1-5-trimethylsilylfuran to <beta> -alkenyl- <gamma> -hydroxybutenolide. The first synthesis of E-neomanoalide from allylchloride was also achieved in short steps by Pd(0) catalized coupling with a <alpha> -silylfuran derivative and reduction.
2. 8,10-dehydro-dehydrologanin, a key intermediate for the synthesis of poly-functional iridoids was synthesized from cis-1,2,3,6-tetrahydrophthalic anhydride. Optically active key intermediate was efficiently synthesized from natural geniposide. Secologanin was efficiently synthesized from key intermediate by the method involving fragmentation reaction of <gamma> -hydroxystannane. Brefeldin A, a macrolide antibiotics was also synthesized by the same method. Penstemide, didrovaltrate, allamandicin and plumericin were synthesized starting from genipin.
3. Terrecyclic acid , antitumor sesquiterpene, was synthesized from (+)- fenchone and the absolute configuration of terrecyclic acid and quadrone was established.
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Report
(1 results)
Research Products
(11 results)
