P-33 Synthetic Study on Yuzurimine-type Alkaloids
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- Hayakawa Ichiro
- Graduate School of Natural Science and Technology, Okayama University
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- Ikeda Masaki
- Graduate School of Natural Science and Technology, Okayama University
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- Niida Keisuke
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Nakashige Yuichi
- Graduate School of Natural Science and Technology, Okayama University
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- Nagayasu Anna
- Graduate School of Natural Science and Technology, Okayama University
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- Nomura Saki
- Graduate School of Natural Science and Technology, Okayama University
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- Saito Keita
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Kigoshi Hideo
- Graduate School of Pure and Applied Sciences, University of Tsukuba
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- Sakakura Akira
- Graduate School of Natural Science and Technology, Okayama University
Bibliographic Information
- Other Title
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- P-33 ユズリハアルカロイド・ユズリミン類の合成研究
Abstract
Yuzurimine-type alkaloids make up a sub-family of Daphniphyllum alkaloids isolated from Daphniphyllum macropodum by Hirata and co-workers. The structural feature of yuzurimine-type alkaloids is the [6-7-5-5] tetracarbocyclic core framework fused with an indolizidine unit. In this presentation, we describe our construction of the [6-7-5-5] tetracarbocyclic core, all the carbocyclic framework of yuzurimine-type alkaloids by using unique in situ intramolecular Wittig reaction and Sm-mediated cyclization as key steps. A plausible reaction pathway for the formation of the seven-membered enone 27 via intramolecular Wittig reaction can be explained as follows. Alkylation of iodide 23 with (methoxycarbonylmethylene)tributylphosphorane (15) followed by deprotonation with an excess of phosphorane 15 might afforded ylide 25. Ylide 25 was then cyclized by intramolecular Wittig reaction to afford seven-membered enone 27. Enone 27 was converted into aldehyde 28, which was treated with SmCl2 to afford lactone 29 and tetracyclic compound 30. These compounds 29 and 30 contain the [6-7-5-5] tetracarbocyclic cores of yuzurimine-type alkaloids. Also, we attempted to the construction of the heterocyclic portion of yuzurimine-type alkaloids by using Staudinger reaction, aza-Wittig reaction, and intramolecular SN2 reaction as key steps.
Journal
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- Symposium on the Chemistry of Natural Products, symposium papers
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Symposium on the Chemistry of Natural Products, symposium papers 59 (0), 375-380, 2017
Symposium on the Chemistry of Natural Products Steering Committee
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Details 詳細情報について
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- CRID
- 1390285697597620736
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- NII Article ID
- 130007906327
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- ISSN
- 24331856
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed