2017 Fiscal Year Final Research Report
Studies toward total synthesis of nigricanosides, anti-mitotic agents from a marine green alga, aiming at the elucidation of the pharmacophore
| Project/Area Number |
15K01794
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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 |
Biomolecular chemistry
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| Research Institution | Akita University |
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Principal Investigator |
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| Research Collaborator |
TSUNODA Takayuki
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Keywords | 全合成研究 / クライゼン転位 / 鎖状エーテル / 有糸分裂阻害剤 / 1,4-ジアルコキシ-2-ブテン / ヘンリー反応 / ラジカル脱離反応 / 立体選択的合成 |
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| Outline of Final Research Achievements |
Nigricanoseides, isolated from the green alga Avrainvillea nigricans, belong to a monogalactosyldiacylglycerol family and were reported to exhibit potent growth inhibition against cancer cells due to their anti-mitotic activity. Based on the absolute stereochemistry of nigricanoside A dimethyl ester elucidated by Ready and coworkers in 2015, a new convergent total synthesis of the compound was planned to realize the efficient supply. So far, the ether-cross-linkages between the upper and the lower fatty acid chains and between the lower fatty acid chain and the galactose moiety have been constructed based on chirality transferring Ireland-Claisen rearrangement. A prototype synthetic route to the right-half segment of nigricanoside A dimethyl ester has also been developed. Furthermore, a construction method for the C9'-C10' double bond has been developed by use of model compounds having ether bonds adjacent to the reaction centers.
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| Free Research Field |
天然物合成化学
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