Synthesis of the core ring system of awajanomycin from N-Boc-3-methoxycarbonyl-2-pyridinone

Kou Hiroya, Kei Kawamoto, Kiyofumi Inamoto, Takao Sakamoto, Takayuki Doi

研究成果: Article査読

10 被引用数 (Scopus)

抄録

Awajanomycin, which was isolated from marine-derived fungus, possesses unique structural features and cytotoxic activity against A549 cells. Due to its unique structure, no total synthesis has yet been reported, and neither the relative stereochemistry nor the absolute configuration has been determined. We report the synthesis of the core ring system of awajanomycin, which includes: (i) regioselective addition of the acetate unit onto C4-position of N-Boc-3-methoxycarbonyl-2-pyridinone; (ii) stereoselective installation of a hydroxyl group on C3-position; and (iii) stereo- and regioselective epoxide-opening reaction by Me3Al.

本文言語English
ページ(範囲)2115-2118
ページ数4
ジャーナルTetrahedron Letters
50
18
DOI
出版ステータスPublished - 2009 5 6

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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