Synthesis and Formation Mechanism of a Compound with an Unprecedented Skeleton : Dodecahydro-4,10:5,9-diepoxydipyrrolo[3,4-b:3',4'-f][1,5]diazocine

• Shinoda Misaki

  Showa Pharmaceutical University

• Morita Nobuyoshi

  Showa Pharmaceutical University

• Tanaka, III Kosaku

  Showa Pharmaceutical University

• Hashimoto Yoshimitsu

  Showa Pharmaceutical University

• Ban Shintaro

  Showa Pharmaceutical University

• Tamura Osamu

  Showa Pharmaceutical University

書誌事項

タイトル別名

• Synthesis and Formation Mechanism of a Compound with an Unprecedented Skeleton: Dodecahydro-4,10:5,9-diepoxydipyrrolo[3,4-<i>b</i>:3′,4′-<i>f</i>][1,5]diazocine

抄録

The reaction of N-(2-{[(tert-butyldimethylsilyl)oxy]imino}ethyl)-4-methyl-N-(3-phenylprop-2-yn-1-yl)benzenesulfonamide (6b) with BF₃·OEt₂ afforded a compound with an unprecedented dodecahydro-4,10 : 5,9-diepoxydipyrrolo[3,4-b:3′,4′-f][1,5]diazocine skeleton (7) after aqueous work-up. The formation mechanism of meso-7 appears to involve dimerization of the hydrated forms (6aS)-C and (6aR)-C of the initial racemic product 9 via cation B generated by facile protonation at the C3a position of 9. Extensive computational studies revealed that the driving force of the facile hydration of 9 is probably release of the ring strain of 9, which arises in part from the bent sp²-hybridized C3a carbon.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 68 (12), 1238-1243, 2020-12-01

  公益社団法人 日本薬学会

キーワード

• <i>N</i>-boranonitrone
• cycloaddition
• ω-acetylenic <i>O</i>-<i>tert</i>-butyldimethylsilyl oxime
• dodecahydro-4,10 : 5,9-diepoxydipyrrolo[3,4-<i>b</i>:3′,4′-<i>f</i>][1,5]diazocine compound
• ring strain

詳細情報

• CRID: 1391130851443047296
• NII論文ID: 130007948456
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.c20-00561
• ISSN: 13475223
• ISSN: 00092363
• NDL書誌ID: 030781807
• PubMed: 33268656
• Web Site: http://id.ndl.go.jp/bib/030781807
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I030781807
• Web Site: https://www.jstage.jst.go.jp/article/cpb/68/12/68_c20-00561/_pdf
• 本文言語コード: en
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可