Development of novel synthetic reactions based on release of strain energy in small ring system and its application to total syntheses of natural products
Project/Area Number |
22590023
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | Kyoto Pharmaceutical University |
Principal Investigator |
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Co-Investigator(Kenkyū-buntansha) |
KOJIMA Naoto 京都薬科大学, 薬学部, 講師 (90420413)
岩崎 宏樹 京都薬科大学, 薬学部, 助教 (70582592)
小関 稔 京都薬科大学, 薬学部, 助教 (40465597)
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Project Period (FY) |
2010-04-01 – 2013-03-31
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Project Status |
Completed (Fiscal Year 2013)
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Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
|
Keywords | 環歪み / シクロプロパン / 骨格変換反応 / 2-オキソ-2H-ピラン-3-カルボン酸 / ビシクロ[3.1.0]ヘキサン-3-カルボン酸 / ジヒドロ-3aH-シクロペンタ[b]フラン / アダンクチンB / イリド / 反応機構 / シクロブタン / アダンクチンB / 環開裂 / クマリン |
Research Abstract |
A small ring system such as cyclopropane ring and cyclobutane ring is one of the important functional groups to easily ring-open due to their ring strain release in organic synthetic chemistry. The reaction of alfa-pyrone derivatives which have an electron-withdrawing group at the 3-position with dimethylsulfoxonium methylide was examined. Bicycle[3.1.0]hexane derivatives and cyclopentadihydrofuran derivatives were selectively obtained on the basis of difference between substituent groups on the 5-position of alfa-pyrone. Furthermore, a natural product, adunctin B, was synthesized via a key reaction of coumarin which has an electron-withdrawing group at the 3-position with dimethylsulfoxonium methylide.
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Report
(4 results)
Research Products
(44 results)
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[Journal Article] First asymmetric total synthesis of (+)-taiwaniaquinol D and (?)-taiwaniaquinone D by using intramolecular Heck reaction2013
Author(s)
Minoru Ozeki, Megumi Satake, Toshinori Toizume, Shintaro Fukutome, Kenji Arimitsu, Shinzo Hosoi, Tetsuya Kajimoto, Hiroki Iwasaki, Naoto Kojima, Manabu Node, Masayuki Yamashita
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Journal Title
Tetrahedron
Volume: 69
Issue: 19
Pages: 3841-3846
DOI
Related Report
Peer Reviewed
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[Journal Article] Synthesis of (.+-.)-8-Deisopropyladunctin B2012
Author(s)
Sayo Nomura, Kenji Arimitsu, Satoshi Yamaguchi, Yuya Kosuga, Yuko Kakimoto, Takanori Komai, Kazumasa Hasegawa, Akira Nakanishi, Tamami Miyoshi, Hiroki Iwasaki, Minoru Ozeki, Ikuo Kawasaki, Ai Kurume, Shunsaku Ohta, Masayuki Yamashita
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Journal Title
Chemical and Pharmaceutical Bulletin
Volume: 60
Issue: 1
Pages: 94-103
DOI
NAID
ISSN
0009-2363, 1347-5223
Related Report
Peer Reviewed
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[Presentation] Cyclopenta[b]benzofuran-3-one体のtetrahydrodibenzofuran体への環拡大反応2014
Author(s)
山本卓,伊藤健史,原川牧子,宮上康徳,齋藤興輝,松井優子,有光健治,小島直人,岩崎宏樹,小関稔,山下正行
Organizer
日本薬学会第134年会
Place of Presentation
熊本
Related Report
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