2014 Fiscal Year Final Research Report
Synthetic Study for Piperidamycins
| Project/Area Number |
25750381
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Biomolecular chemistry
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| Research Institution | Tohoku University |
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Principal Investigator |
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| Project Period (FY) |
2013-04-01 – 2015-03-31
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| Keywords | 全合成 / デプシペプチド / 抗菌活性 / ピペラジン酸 |
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| Outline of Final Research Achievements |
Synthetic studies of piperidamycin F and JBIR-39 were investigated. Acylation of gamma-hydroxypiperazic acid with acid chloride was efficiently performed in the presence of Sc(OTf)3 to afford the corresponding dipeptide in good yield. Synthesis of oligopiperazic acid structure, followed by removal of the protecting groups furnished the natural product JBIR-39. The structure of JBIR-39 was unequivocally determined, and its absolute configurations were established to be 2S, 6S, 8S, 11R, 16S, 21R, 26S, 27S. Based on the above results, synthesis of pipericamycin F was also investigated and preparation of its macrocyclic structure was carried out by macrolatonization using 2-methyl-6-nitrobenzoic anhydride (MNBA).
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| Free Research Field |
生物分子科学
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