書誌事項
- タイトル別名
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- Total Syntheses of Dimmeric Lycopodium Alkaloid, Complanadines A and B
- ニリョウ タイケイ リコポジウムアルカロイド ・ コンプラナジン A オヨビ B ノ ゼン ゴウセイ
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説明
<p>Our total syntheses of lycopodium alkaloid lycodine (1), and its unsymmetric dimmer complanadines A (3) and B (4) were described. The bicyclo[3.3.1]nonane core structure of lycodine was constructed by regioselective Diels-Alder and intramolecular Mizoroki-Heck reactions. A late-stage coupling reaction of the lycodine units, pyridine N-oxide (+)-17 and aryl bromide (+)-16, through C-H arylation at the C1 position of (+)-17 provided the unsymmetric dimer structure. This strategy significantly simplified the construction of the dimeric architecture and functionalization. Total syntheses of complanadines A (3) and B (4) were achieved by adjusting the oxidation level of the bipyridine mono-N-oxide (+)-18. The diverse utility of this common intermediate (+)-18 suggests a possible biosynthetic pathway of complanadines in nature. Both enantiomers of lycodine (1) and complanadines A (3) and B (4) were prepared in sufficient quantities. The effect on neuron differentiation of PC-12 cells with human astrocytoma cells culture medium was evaluated.</p>
収録刊行物
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- 有機合成化学協会誌
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有機合成化学協会誌 77 (2), 135-144, 2019-02-01
公益社団法人 有機合成化学協会
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詳細情報 詳細情報について
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- CRID
- 1390282763098771712
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- NII論文ID
- 130007596426
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- NII書誌ID
- AN0024521X
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 029510727
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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
- NDL
- Crossref
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- KAKEN
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- 抄録ライセンスフラグ
- 使用不可