Total synthesis of janadolide

Daisuke Ojima, Hitomi Mine, Arihiro Iwasaki, Kiyotake Suenaga

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

The first total synthesis of janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, is described. The synthesis of an unsaturated hydroxycarboxylic acid was effected via the lithiation of vinyl iodide followed by addition to a Weinreb amide with a tert-butyl group and stereoselective 1,2-reduction. The cyclic structure was constructed by macrolactamization at the amide bond between the proline moiety and fatty acid moiety.

Original languageEnglish
Pages (from-to)1360-1362
Number of pages3
JournalTetrahedron Letters
Volume59
Issue number14
DOIs
Publication statusPublished - 2018 Apr 4

Keywords

  • Depsipeptide
  • Macrolactamization
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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