Isolation, Structure, and Total Synthesis of the Marine Macrolide Mangrolide D

Junyu Gong, Wei Li, Peng Fu, John Macmillan, Jef K. De Brabander

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The isolation, characterization, and total synthesis of the macrocyclic polyene mangrolide D is reported. A 16-step total synthesis relies on robust Suzuki and ring-closing metathesis reactions, and an iron-catalyzed hydroazidation of an exomethylene substituted tetrahydropyran as a key step for the synthesis of the appended 4-epi-vancosamine sugar. Although mangrolide D did not display antibiotic activity, this work should prove enabling toward the synthesis of the antitubercular tiacumicins which display a virtually identical macrocyclic backbone.

Original languageEnglish (US)
Pages (from-to)2957-2961
Number of pages5
JournalOrganic Letters
Volume21
Issue number8
DOIs
StatePublished - Apr 19 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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