| Project/Area Number |
15K17853
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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 |
Synthetic chemistry
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| Research Institution | Meiji University (2016)
Tokyo Institute of Technology (2015) |
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Principal Investigator |
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| Project Period (FY) |
2015-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
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| Keywords | ホスラクトマイシン / 効率的合成 / キレーションコントロール / ロイストロダクシン / 立体選択的合成 |
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| Outline of Final Research Achievements |
We have investigated the synthesis of phoslactomycin I-j having an ester group in the cyclohexyl moiety. Three chiral centers of C8-C11 were constructed by chelation controlled addition of Grignard reagent to aldehyde and asymmetric hydrogen transfer reaction of acetylene ketone. After removal of the asymmetric auxiliary group, unsaturated ester was obtained by Z selective HWE reaction reported by Ando et al. Subsequently, the unsaturated ester moiety was constructed by cyclization reaction with a titanium catalyst to give key intermediate. Finally, total synthesis of phoslactomycin I-j was achieved by sequentially introducing phosphate group and amino group into this key intermediate.
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