Total Synthesis of (+)-ascospiroketals A,B and Determination of there Absolute Configurations
| Project/Area Number |
26460028
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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 |
Chemical pharmacy
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| Research Institution | Tokushima Bunri University |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
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| Keywords | ascospiroketal / 1,4-addition reaction / asymmetric aldol / diastereo selective / ganmma-lactone / beta-lactone / decarboxylation / organic synthesis / asymmetric / synthesis / natural product / polyketide / 1,4-addition / aldol reaction / 結核 / 不斉1,4-付加 / 不斉アルドール / β-ラクトン / 連続不斉中心 / 不斉四級炭素 / 天然物合成 / ascospiroketals / tetraalkylated / all-carbon / quaternary center |
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| Outline of Final Research Achievements |
The synthesis of (+)-ascospiroketal B commenced from 2-propyn-1-ol, namely, Negishi iodomethylation of 2-propyn-1-ol followed by protection of hydroxy group by TBDPS and coupling reaction with (S)-2-phenyloxazolidinone accompanied insertion of CO catalyzed by Pd(PPh3)4 afforded 1. Then 1 was treated with vinyl copper reagent and converted to 2 in high diastereoselectivity. The aldol reaction of 2 accompanied by removal of oxazolidinone moiety to form b-lactone ring gave β-lactone 3 as a single isomer. Methylation of 3 with MeLi followed by ozonolysis and PDC oxidation produced γ-lactone 5 in good yields. Although Bayer-Viliger oxidation of 5 with usual reagent such as mCPBA did not proceeded due to the steric strain around methylketone．
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Report
(4 results)
Research Products
(12 results)
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[Journal Article] Bakuchiol Is a Phenolic Isoprenoid with Novel Enantiomer-​selective Anti-​influenza A Virus Activity Involving Nrf2 Activation2015
Author(s)
Shoji, Masaki; Arakaki, Yumie; Esumi, Tomoyuki; Kohnomi, Shuntaro; Yamamoto, Chihiro; Suzuki, Yutaka; Takahashi, Etsuhisa; Konishi, Shiro; Kido, Hiroshi; Kuzuhara, Takashi
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Journal Title
Journal of Biological Chemistry
Volume: 290
Issue: 46
Pages: 28001-28017
DOI
NAID
Related Report
Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
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[Journal Article] Chemical diversity of vibsane-type diterpenoids and neurotrophic activity and synthesis of neovibsanin. Kubo, M.; Esumi, T.; Imagawa, H.; Fukuyama, Y. Studies in Natural Products chemistry 2014, 43, 41-78. ② Seed dormancy breaking diterpenoids from the liverwort Plagiochila sciophila and their differentiation inducing activity in human promyelocytic leukemia HL-60 cells.2014
Author(s)
Kenmoku, H.; Tada, H.; Oogushi, M.; Esumi, T.; Takahashi, H.; Noji, H.; Sassa, M.; Toyota, M.; Asakawa, Y.
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Journal Title
Natural Product Communications
Volume: 7
Issue: 7
Pages: 915-920
DOI
Related Report
Peer Reviewed / Open Access / Acknowledgement Compliant
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