2011 Fiscal Year Final Research Report
Enantioselective total synthesis of(+)-Hydroxyapparicine, potent antimalarial indole alkaloid.
| Project/Area Number |
22790017
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Kitasato University |
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Principal Investigator |
HIROSE Tomoyasu 北里大学, 大学院・感染制御科学府, 准教授 (00370156)
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| Project Period (FY) |
2010 – 2011
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| Keywords | 有機化学 |
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| Research Abstract |
Hydroxyapparicine was isolated from Tabernaemontana dichotoma in 1984.Then, the relative stereochemistry was proposed that recorded spectral data. However, C15 stereochemistry was not showed. Therefore, absolute stereochemistry of Hydroxyapparicine has never determined. Structure fearture of hydroxyapparicine is 1-azabicyclo[4.2.2] decane and C16 chiral tertiary alchol moiety connected indole 2-position. Moreover, tertiary alchol moiety is unstable under acidic conditions. It was easliy dedydration of similar compound. From synthetic standpiont, synthesis of pseudo-aminal type alkaloids need to novel method under mild conditions. Herein, we repored the stereoselective total synthsis and determination of absolute stereochemistry of 16R-hydroxy-16, 22-dihydroapparicine(Hydroxyapparicine).
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Research Products
(15 results)
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[Journal Article] Solution-phase total synthesis of the hydrophilic natural product argifin using 3, 4, 5-tris(octadecyloxy) benzyl tag2011
Author(s)
Tomoyasu Hirose, Takako Kasai, Takafumi Akimoto, Ayako Endo, Akihiro Sugawara, Kazuo Nagasawa, Kazuro Shiomi, Satoshi Omura, Toshiaki Sunazuka
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Journal Title
Tetrahedron
Volume: Vol.67
Pages: 6633-6643
DOI
Peer Reviewed
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[Journal Article] NMR spectroscopy and computational analysis of interaction between Serratia marcescens chitinase B and a dipeptide derived from natural-product cyclopentapeptide chitinase inhibitor argifin2010
Author(s)
Hiroaki Gouda, Toshiaki Sunazuka, Tomoyasu Hirose, Kanami Iguchi, Noriyuki Yamaotsu, Akihiro Sugawara, Yoshihiko Noguchi, Yoshifumi Saito, Tsuyoshi Yamamoto, Takeshi Watanabe, Kazuro Shiomi, Satoshi Omura, Shuichi Hirono
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Journal Title
Bioorg. Med. Chem.
Volume: Vol.18
Pages: 5835-5844
DOI
Peer Reviewed
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[Presentation] Chitinase inhibitors : Extraction of the active framework from natural argifin and use of in situ click chemistry2001
Author(s)
Tomoyasu Hirose, Akihiro Sugawara, Ayako Endo, Tsuyoshi Yamamoto, Kzuro Shiomi, Takeshi Watanabe, K. Barry Sharpless, Satoshi Omura, Toshiaki Sunazuka
Organizer
242nd American Chemical Society National Meeting
Place of Presentation
Denver, Colorado, USA
Year and Date
20010828-0901
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