Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides

Gang He, Shu Yu Zhang, William A. Nack, Ryan Pearson, Javon Rabb-Lynch, Gong Chen

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

To access the key Ile-Hpa pseudodipeptide motif in hibispeptins, a series of bidentate carboxamide-based auxiliary groups have been explored to facilitate the palladium-catalyzed arylation of unactivated γ-C(sp3)-H bonds of Ile precursor with aryl iodides. A new pyridylmethylamine-based auxiliary group PR is introduced, which permits the use of more sterically hindered ortho-substituted aryl iodide substrates and can be removed under mild conditions. Pd-catalyzed PR-directed γ-C(sp3)-H arylation enabled the first total synthesis of hibispeptin A.

Original languageEnglish (US)
Pages (from-to)6488-6491
Number of pages4
JournalOrganic Letters
Volume16
Issue number24
DOIs
StatePublished - Dec 19 2014

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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