Total Synthesis of Ellagitannins via Sequential Site-Selective Functionalization of Unprotected D-Glucose

• Takeuchi Hironori

  Institute for Chemical Research, Kyoto University

• Ueda Yoshihiro

  Institute for Chemical Research, Kyoto University

• Furuta Takumi

  Institute for Chemical Research, Kyoto University

• Kawabata Takeo

  Institute for Chemical Research, Kyoto University

書誌事項

タイトル別名

• Total Synthesis of Ellagitannins <i>via</i> Sequential Site-Selective Functionalization of Unprotected D-Glucose

抄録

A short-step total synthesis of the natural glycosides pterocarinin C and tellimagrandin II (eugeniin) has been performed by sequential and site-selective functionalization of free hydroxy groups of unprotected D-glucose. The key reactions are β-selective glycosidation of a gallic acid derivative using unprotected D-glucose as a glycosyl donor and catalyst-controlled site-selective introduction of a galloyl group into the inherently less reactive hydroxy group of the glucoside.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 65 (1), 25-32, 2017

  公益社団法人 日本薬学会

キーワード

• site-selectivity
• organocatalyst
• ellagitannin
• chemo-selectivity
• glycosylation unconventional retrosynthesis

詳細情報

• CRID: 1390001204177796224
• NII論文ID: 130005187627
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c16-00436
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 027819906
• PubMed: 28049912
• Web Site: http://id.ndl.go.jp/bib/027819906
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I027819906
• Web Site: https://www.jstage.jst.go.jp/article/cpb/65/1/65_c16-00436/_pdf
• 本文言語コード: en
• データソース種別:
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