2007 Fiscal Year Final Research Report Summary
EFFICIENT SYNTHESIS OF BIOACTIVE NATURAL PRODUCTS EMPLOYING PALLADIUM-CATALYZED CYCLOALKENYLATION AS A KEY STEP
| Project/Area Number |
18390007
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Osaka Prefecture University |
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Principal Investigator |
TOYOTA Masahiro Osaka Prefecture University, GRADUATE SCHOOL OF SCIENCE, PROFESSOR (10217573)
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| Project Period (FY) |
2006 – 2007
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| Keywords | bioactive natural product / quadrone / C_<20> gibberellin / trans-hydridane / cross conjugate / bicycle[3.2.1]octane / intramolecular Diels-Alder / GA_<112> |
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| Research Abstract |
The aim of this research is to investigate total syntheses of bioactive natural products, such as quadron and C_<20> gibberellins, employing the palladium-catalyzed cycloalkenylaton developed by the author as a key step.
(1) Synthetic Studies on Antitumor agent Quadrone Synthesis
The author has succeeded in synthesizing the basic carbon skeleton of quadrone using the palladium-catalyzed cyclolakenylation of the cross conjugated silyl enol ether possessing an allyl group at one of the angular position of the trans-hydrindane.
(2) Synthetic Studies on Plant Regulator Hormone C_<20> Gibberellin Synthesis
First of all, the CD ring system, bycyclo [3.2.1] octane, was constructed using the palladium-catalyzed cycloalkenylation as the first key steps. After introduction of the diene and dienophile parts on the bicyclo [3.2.1]-octane ring compound, the intramolecular Diels-Alder reaction of it was performed to give rise to the desired penta cyclic compound as a single stereoisomer. Functional group manipulation of the cyclization product furnished(-)-GA_<112>.
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