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

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2115-2118
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number18
DOIs
Publication statusPublished - 2009 May 6

Keywords

  • 2-Pyridinone
  • Awajanomycin
  • Conjugate addition
  • Silyl ketene acetal
  • Trimethylaluminum

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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