書誌事項
- タイトル別名
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- Synthesis of Ellagitannins Containing Axial-Rich Glucose
- アキシアル・リッチなグルコースを有するエラジタンニンの合成
- アキシアル ・ リッチ ナ グルコース オ ユウスル エラジタンニン ノ ゴウセイ
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抄録
Ellagitannins are a biologically and structurally diverse class of natural products. The structure typically consists of galloyl and hexahydroxydiphenoyl (HHDP) group(s) esterified to glucose. The pyranose ring of the glucose moiety can even be in the axial-rich conformation when the HHDP group bridges the discontiguous hydroxy groups. We here described first total syntheses of two “axial-rich ellagitannins,”(−)-corilagin and (+)-davidiin, which have the HHDP bridge between 3- and 6-oxygens and between 1- and 6-oxygnens, respectively. In the synthesis of corilagin, the 3,6-bridge was constructed through a temporary ring-opening strategy. With this strategy, three synthetic method of the HHDP group were investigated. The total synthesis was achieved using originally developed method that is the CuCl2-n-BuNH2 mediated coupling of 4-O-benzylated gallates. The 1,6-bridge in davidiin was also constructed by this method with conformational locked strategy relying on the steric repulsion of bulky silyl groups.
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 71 (10), 1051-1060, 2013
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
- 1390001205340196096
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- NII論文ID
- 10031203357
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- NII書誌ID
- AN0024521X
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- COI
- 1:CAS:528:DC%2BC3sXhs1Oiu7vL
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- ISSN
- 18836526
- 00379980
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- NDL書誌ID
- 024935743
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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
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- 抄録ライセンスフラグ
- 使用不可