Total synthesis of verruculogen and fumitremorgin a enabled by ligand-controlled C-H borylation

Yu Feng, Dane Holte, Jochen Zoller, Shigenobu Umemiya, Leah R. Simke, Phil S. Baran

Research output: Contribution to journalArticle

105 Citations (Scopus)

Abstract

Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.

Original languageEnglish
Pages (from-to)10160-10163
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number32
DOIs
Publication statusPublished - 2015 Aug 19

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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