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- 横山 祐作
- 東邦大学薬学部薬品製造学教室
書誌事項
- タイトル別名
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- Development of Unprotected Syntheses in Aqueous Media
- ミズ オ ヨウバイ ト シタ ムホゴ ゴウセイ ハンノウ ノ カイハツ
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抄録
Introduction of carbon side chain at C3-position of indole ring was accomplished by using Pd-catalyzed allylation and vinylation. The selective vinylation at C3-position of 4-bromoindole was applied to the synthesis of optically active 4-bromotryptophan derivatives, which was used as a starting material for the synthesis of several optically active ergot alkaloids, which were clavicipitic acids, chanoclavine-I, costacalvine, and 1,1-dimethylallyltryptophan (DMAT). The three-step synthesis of optically active clavicipitic acids were accomplished without using a protecting group starting from 4-bromoindole and dl-serine. Some new synthetic reactions using unprotected amino acids were developed. Those were the biomimetic synthesis of tryptophan, the bromination of free aromatic amino acids, and the Pd-catalyzed N-allylation of free amino acids with allylic alcohol in aqueous media. Unique reactivity of π-allyl palladium complex or η3-(benzyl)palladium complex in aqueous media was found through Pd-catalyzed reaction of anthranilic acid, 2-aminobenzamide, and indole with allylic alcohols or benzyl alcohols, respectively.<br>
収録刊行物
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- 薬学雑誌
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薬学雑誌 133 (2), 249-268, 2013-02-01
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282681103713536
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- NII論文ID
- 130003361912
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- NII書誌ID
- AN00284903
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- COI
- 1:STN:280:DC%2BC3szksVKrsw%3D%3D
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- ISSN
- 13475231
- 00316903
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- NDL書誌ID
- 024258472
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- PubMed
- 23370521
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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
- PubMed
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可