Ｐｉｎｎａｔｏｘｉｎ　Ａの全合成

• 長澤 和夫

  ハーバード大学化学生物化学科 理化学研究所有機合成化学研究室

書誌事項

タイトル別名

• Total Synthesis of Pinnatoxin A.
• Pinnatoxin A ノ ゼンゴウセイ

抄録

The first total synthesis of pinnatoxin A (1), a Ca²⁺-channel activator isolated in 1995 by Uemura and co-workers from the shellfish Pinna muricata, is reported. The synthetic plan was based on Uemura's biosynthetic proposal, and consists of an intramolecular Diels-Alder reaction for construction of the G-ring as well as the macrocycle, followed by imine formation to establish the 6, 7-spiro-ring system. During this investigation, factors controlling the stereochemistry of the BCD bis-spiroketal ring system were investigated, and the chemoselectivity and efficiency of the Ni (II) /Cr (II) -mediated coupling protocol were demonstrated. This synthesis has also established the absolute stereochemistry of natural pinnatoxin A as the antipode of structure 1.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 58 (9), 877-886, 2000

  公益社団法人 有機合成化学協会

キーワード

• pinnatoxin A
• Ca-channel activator
• intramolecular Diels-Alder reaction
• biosynthesis
• spiro imine
• Ni (II) /Cr (II) mediated coupling
• epimerization

詳細情報

• CRID: 1390282680254197376
• NII論文ID: 10008821884
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.58.877
• COI: 1:CAS:528:DC%2BD3cXmtlKgt7s%3D
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 5474971
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I5474971
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可