Ｐａｐｕｌａｃａｎｄｉｎ　Ｄの全合成

• 小林 徹也

  CV Therapeutics, Inc.

• Regens Christopher S.

  University of Illinois at Urbana -Champaign

• Denmark Scott E.

  University of Illinois at Urbana -Champaign

書誌事項

タイトル別名

• Total Synthesis of Papulacandin D
• Papulacandin D ノ ゼンゴウセイ

抄録

A total synthesis of (+)-papulacandin D which shows an antifungal activity is reported. The molecule is one of the members of C-arylglycoside isolated from Papularia spherosperma. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the aryl glycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. This highly convergent synthesis was accomplished in 31 steps overall from commercial starting materials.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 66 (6), 616-628, 2008

  公益社団法人 有機合成化学協会

キーワード

• papulacandin
• C-arylglycoside
• total synthesis
• organo-silanol cross-coupling reaction
• palladium
• enantioselective Lewis base catalysis
• asymmetric allylation
• cross-metathesis

詳細情報

• CRID: 1390282680287601664
• NII論文ID: 10021175633
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.66.616
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 9545098
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I9545098
• 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