Total synthesis of janadolide

Daisuke Ojima, Hitomi Mine, Arihiro Iwasaki, Kiyotake Suenaga

Research output: Contribution to journalArticle

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
JournalTetrahedron Letters
DOIs
Publication statusAccepted/In press - 2018 Jan 1

Fingerprint

Amides
Polyketides
Cyclic Peptides
Proline
Fatty Acids
Acids
vinyl iodide

Keywords

  • Depsipeptide
  • Macrolactamization
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Total synthesis of janadolide. / Ojima, Daisuke; Mine, Hitomi; Iwasaki, Arihiro; Suenaga, Kiyotake.

In: Tetrahedron Letters, 01.01.2018.

Research output: Contribution to journalArticle

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