2013 Fiscal Year Final Research Report
Development of a method for preparation of optically active compounds under thermodynamical equilibrium conditions based on inclusion complexation
| Project/Area Number |
23590034
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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 |
KAKU Hiroto 徳島文理大学, 薬学部, 准教授 (90299339)
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| Project Period (FY) |
2011 – 2013
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| Keywords | 精密分子認識 / 包接錯体 / 光学分割 / テトラフェニレン誘導体 / デラセミ化 / フェネチルアミン類 / X線結晶解析 |
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| Research Abstract |
Racemic 2,7,10,15-tetrahydroxytetraphenylene (THTP) was synthesized starting from 3-bromoanisole in 4 steps (overall yield 45%). Optical resolution of the racemic THTP was achieved by include complexation using (S)-phenethylamine to afford (-)-THTP, which could be used as a host molecule for optical resolution of racemic phenethylamine to (S)-phenethylamine. An X-ray crystallographic study elucidated that the host molecules THTP ingeniously included the guest molecule via hydrogen bonding and van der Waals interactions. Furthermore, the inclusion complex consisted of (-)-THTP, (S)-phenethylamine, and toluene in a 1 : 2 : 1 ratio, respectively.
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[Journal Article] Xanthouroleuconaphin : a yellowish pigment from the aphid Uroleucon nigrotuberculatum and its total synthesis2013
Author(s)
Nishimura, T.; Horikawa, M.; Yamada, K.; Sogabe, A.; Nishii, T.; Kaku, H.; Inai, M.; Tanaka, M.; Takahashi, S.; Tsunoda, T.
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Journal Title
Tetrahedron
Volume: 69
Pages: 1808-1814
DOI
Peer Reviewed
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[Journal Article] Promotion of Asymmetric Aza-Claisen Rearrangement of N-Allylic Carboxamides Using Excess Base2011
Author(s)
Yoshizuka, M.; Nishii, T.; Sasaki, H.: Kitakado, J.; Ishigaki, N.; Okugawa, S.; Kaku, H.; Horikawa, M.; Inai, M.; Tsunoda, T.
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Journal Title
Synlett
Volume: 20
Pages: 2967-2970
DOI
Peer Reviewed
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[Journal Article] Viridaphin A1 Glucoside, a Green Pigment Possessing Cytotoxicity and Antibacterial Activity from the Aphid Megoura crassicauda Mordvilko2011
Author(s)
Horikawa, M.; Hoshiyama, T.; Matsuzawa, M.; Shugyo, T.; Tanaka, M.; Suzuki, S.; Sato, M.; Ito, T.; Asakawa, Y.; Kaku, H.; Nishii, T.; Inai, M.; Takahashi, S.; Tsunoda, T.
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Journal Title
J. Nat. Prod
Volume: 74(8)
Pages: 1812-1816
DOI
Peer Reviewed
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[Presentation] 不斉分子認識を基盤とする光学活性2,3-及び2,5-ジ置換環状ケトン類の効率的供給法(An Efficient Method for Preparation of Optically Active 2,3- and 2,5-Disubstituted Cyclohexanones under Asymmetric Inclusion Complexation)2012
Author(s)
加来裕人,谷由紀子,上原李佳子,西谷亮二,稲井誠,堀川美津代,角田鉄人
Organizer
Symposium on Molecular Chirality ASIA 2012
Place of Presentation
福岡
Year and Date
2012-05-17
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