A new synthetic method of bioactive terpene indole alkaloids
| Project/Area Number |
24380063
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Partial Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Nagoya University |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
Nakazaki Atsuo 名古屋大学, 大学院生命農学研究科, 准教授 (00366428)
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| Project Period (FY) |
2012-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥18,070,000 (Direct Cost: ¥13,900,000、Indirect Cost: ¥4,170,000)
Fiscal Year 2015: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2014: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2013: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2012: ¥7,150,000 (Direct Cost: ¥5,500,000、Indirect Cost: ¥1,650,000)
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| Keywords | インドールアルカロイド / 有機合成 / 天然物合成 / 連続環化反応 / セスペンドール / 構造決定 / 光学活性体 / 不斉合成 / レカインドール / 立体配置決定 |
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| Outline of Final Research Achievements |
This research has focused on development of an efficient synthetic route of sespendole, a naturally occurring indole alkaloid including complex terpene structure. We plan that segment 1 including the aromatic moiety and segment 2 of the terpene moiety are separately synthesized, and then coupled together followed by cyclization of the B and C rings at the same time. Two possible diastereomers of the segment 1 were synthesized and then transformed to indole compounds. Comparison of NMR spectra of those indoles and sespendole determined relative stereochemistry of the epoxyalcohol to be syn. Investigation of coupling between two segments and tandem cyclization revealed that the former coupling was realized under a condition of the Sonogashira coupling and the latter tandem cyclization was effectively catalyzed with a Cu or Pd catalyst.
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Report
(5 results)
Research Products
(86 results)
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[Journal Article] Structural Study on a Naturally Occurring Terphenyl Quinone2013
Author(s)
Nakazaki, A.; Huang, W.-Y.; Koga, K.; Yingyongnarongkul, B.; Boonsombat, J.; Sawayama, Y.; Tsujimoto, T.; Nishikawa, T.
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Journal Title
Bioscience, Biotechnology, and Biochemistry
Volume: 77
Issue: 7
Pages: 1529-1532
DOI
NAID
ISSN
0916-8451, 1347-6947
Related Report
Peer Reviewed
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[Presentation] Synthesis of biologically active steroid-derived compounds from an edible mushroom.2015
Author(s)
Toshio Nishikawa, Yoshiki Nakane, Atsuo Nakazaki, Takuya Imazu, Shouta Tokoro, Ryo Sakakibara, Masaatsu Adachi, Keiichi Konoki, Mari Yotsu-Yamashita
Organizer
The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
Place of Presentation
Honolulu, Hawaii, USA
Year and Date
2015-12-15
Related Report
Int'l Joint Research / Invited
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[Presentation] Synthesis and biological activities of guanidine-containing natural products.2015
Author(s)
Toshio Nishikawa, Yoshiki Nakane, Atsuo Nakazaki, Takuya Imazu, Shouta Tokoro, Ryo Sakakibara, Masaatsu Adachi, Keiichi Konoki, Mari Yotsu-Yamashita
Organizer
The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
Place of Presentation
Honolulu, Hawaii, USA
Year and Date
2015-12-15
Related Report
Int'l Joint Research
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[Presentation] イリドイド類の合成研究2014
Author(s)
宮澤 悠、安立昌篤、室岡孝信、宮崎雅雄、西川俊夫
Organizer
日本農芸化学会中部支部第171回例会
Place of Presentation
名古屋
Year and Date
2014-10-11
Related Report
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[Presentation] イリドイド類の合成研究2014
Author(s)
宮澤 悠、安立昌篤、室岡孝信、宮崎雅雄、西川俊夫
Organizer
第49回天然物化学談話会
Place of Presentation
岡山
Year and Date
2014-07-02 – 2014-07-04
Related Report
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