2013 Fiscal Year Final Research Report
Synthetic studies of natural products with a quaternary stereocenter attahced to nitrogen
| Project/Area Number |
23510258
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Living organism molecular science
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| Research Institution | Kochi University |
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Principal Investigator |
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| Co-Investigator(Renkei-kenkyūsha) |
MASUDA Toshiya 徳島大学, 総合科学部, 教授 (10219339)
KOTSUKI Hiyoshizo 高知大学, 総合研究センター, 特任教授 (80093954)
NAKANO Keiji 高知大学, 教育研究部自然科学系, 准教授 (50399747)
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| Project Period (FY) |
2011 – 2013
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| Keywords | 全合成 / 天然物化学 / 有機合成 / 含窒素天然物 / 転位反応 / 海洋天然物 / テルペン / アルカロイド |
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| Research Abstract |
Sigmatropic rearrangement of allyl cyanate offers an effcient transformation of the allyl alcohols into the allyl amines with high stereospecific manner. We have planned to apply this rearrangement to the synthesis of natural products. Synthetic efforts focused on the synthesis of marine natural products, such as geranyllinaloisocyanide and manzacidins. As a result, the first non-racemic synthesis of geranyllinaloisocyanide, starting with lactic acid methyl ester, has been accomplished by exploiting a sigmatropic rearrangement of allyl cyanate. An efficient synthetic method for stereoselective construction of asymmetric quaternary carbon stereocenters, bearing nitrogen in the form of Boc-protected allyl amines, has been developed. This methodology is employed in the synthesis of marine alkaloids, manzacidin A and C.
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