2010 Fiscal Year Final Research Report
Studies toward the total synthesis of marine natural products having an azaspiro ring system
| Project/Area Number |
20590001
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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 |
Chemical pharmacy
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| Research Institution | Hokkaido University |
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Principal Investigator |
NAKAMURA Seiichi Hokkaido University, 大学院・薬学研究科, 教授 (90261320)
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| Project Period (FY) |
2008 – 2010
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| Keywords | スピロリド類 / ムスカリン受容体阻害作用 / [6,5,5]-ジスピロケタール / 分子内ヘテロMichael反応 / ヘミケタールアルコキシド / 立体エネルギー / 渡環型反応 / Diels-Alder反応 |
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| Research Abstract |
Toward the total synthesis of spirolides, marine natural products with an azaspirocyclic system, the construction of E and BCD ring systems of these molecules have been explored. Diels-Alder reaction of the diene, prepared from L-glutamic acid, with a 7-membered α-methylene lactone exhibited complete regioselectivity and modest exo and diastereoface selectivity to provide the desired exo cycloadduct as the major product. Since all attempts to obtain the desired dispiroketal isomer from an acyclic precursor by tandem double hemiketal formation/hetero-Michael addition sequence met with failure, we turned our attention to the transannular reaction, and designed and synthesized a macrocyclic substrate.
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