2002 Fiscal Year Final Research Report Summary
Research for the function of nuclear receptors using 9Z-retinoic acid analogs
| Project/Area Number |
12672165
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
医薬分子機能学
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| Research Institution | Kobe Pharmaceutical University |
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Principal Investigator |
ITO Masayoshi Kobe Pharm Univ., Professor, 薬学部, 教授 (20068331)
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| Co-Investigator(Kenkyū-buntansha) |
WADA Akimori Kobe Pharm Univ., Associate Professor, 薬学部, 助教授 (80158683)
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| Project Period (FY) |
2000 – 2002
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| Keywords | retinoic acid analog / nuclear receptor / RXR / RAR / Stereoselective synthesis / coupling reaction / stannyl olefin / enol triflate |
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| Research Abstract |
Stereoselective synthesis of di- and tri-substituted olefins was investigated.
A Palladium catalyzed cross coupling reactions of vinyl triflate and Z-alkenyl stannanes afforded stereoselectively the trisubstituted Z-olefins in high yields, which were converted to the corresponding 9Z-retinoic acids via Emmons-Horner reaction and subsequent basic hydrolysis in excellent yields.
On the contrary, a palladium catalyzed cross coupling reactions of E-tetraenyl stannanes, derived from the terminal acetylenes, with E- or Z-vinyl triflates afforded the novel method for the stereoselective synthesis of all-E-, 13Z- and 9Z- retinoic acid esters in good yields. Applying this methodology, 13-substituted all-E- and 9Z- retinoic acids were prepared in satisfactory yields.
Now, the structural and biological activity relationship of these analogs is in progress.
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