P-33 ユズリハアルカロイド・ユズリミン類の合成研究
書誌事項
- タイトル別名
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- P-33 Synthetic Study on Yuzurimine-type Alkaloids
抄録
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.
収録刊行物
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 59 (0), 375-380, 2017
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390285697597620736
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- NII論文ID
- 130007906327
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可