分子内<i>C</i>-グリコシル化反応を利用したPolygalolide Aの全合成

• 安立 昌篤

  名古屋大学大学院生命農学研究科

書誌事項

タイトル別名

• Total Synthesis of Polygalolide A by Intramolecular C-Glycosylation
• 分子内C-グリコシル化反応を利用したPolygalolide Aの全合成
• ブンシ ナイ C-グリコシルカ ハンノウ オ リヨウ シタ Polygalolide A ノ ゼン ゴウセイ

抄録

Total synyhesis of polygalolide A, a secondary metabolite isolated from a Chinese medicinal plant, was achieved. In order to construct an oxabicyclo[3.2.1] core skeleton, we have developed an intramolecular Ferrier-type C-glycosylation of a glucal modified with siloxyfuran as an internal nucleophile. Although the conditions found in the model experiments did not undergo the C-glycosylation, further examination led us to find that combination of TMSOTf and 2,4,6-collidine was the best condition, giving oxabicyclo[3.2.1]octene with correct quaternary stereogenic centers in high yield. The successful production of the single diastereomer indicated that the siloxy group at the C-3 position played a crucial role for the stereocontrol. After transformation into tetracyclic intermediate, a phenolic moiety was finally introduced by Mukaiyama aldol reaction to furnish polygalolide A.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 73 (6), 607-615, 2015

  公益社団法人 有機合成化学協会

キーワード

• asymmetric synthesis
• glucal
• <i>C</i>-glycosylation
• natural products
• polygalolide
• siloxyfuran
• total synthesis

詳細情報

• CRID: 1390282680318194176
• NII論文ID: 130005088786
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.73.607
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 026544907
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I026544907
• 本文言語コード: ja
• データソース種別:
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