Total Synthesis of Tambromycin Enabled by Indole C-H Functionalization

Galen P. Miley, Jennifer C. Rote, Richard B. Silverman, Neil L. Kelleher, Regan J. Thomson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

The total synthesis of tambromycin (1), a recently isolated tetrapeptide, is reported. This unusual natural product possesses a highly modified tryptophan-derived indole fragment fused to an α-methylserine-derived oxazoline ring, and a unique noncanonical amino acid residue named tambroline (11). A convergent synthesis of tambromycin was achieved by a 13-step route that leveraged recent developments in the field of C-H functionalization to prepare the complex indole fragment, as well as an efficient synthesis of tambroline that featured a diastereoselective amination of homoproline.

Original languageEnglish (US)
Pages (from-to)2369-2373
Number of pages5
JournalOrganic Letters
Volume20
Issue number8
DOIs
StatePublished - Apr 20 2018

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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