A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids

Eric R. Miller, M. Todd Hovey, Karl A. Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

Abstract

We report a concise, enantioselective synthesis of the yohimbine alkaloids (-)-rauwolscine and (-)-alloyohimbane. The key transformation involves a highly enantio- and diastereoselective NHC-catalyzed dimerization and an amidation/N-acyliminium ion cyclization sequence to furnish four of the five requisite rings and three of the five stereocenters in two operations. This route also provides efficient access to all four diastereomeric arrangements of the core stereotriad of the yohimbine alkaloids from a common intermediate. This platform approach in combination with the ability to access both enantiomers from the carbene-catalyzed reaction is a powerful strategy that can produce a wide range of complex alkaloids and related structures for future biomedical investigations.

Original languageEnglish (US)
Pages (from-to)2187-2192
Number of pages6
JournalJournal of the American Chemical Society
Volume142
Issue number5
DOIs
StatePublished - Feb 5 2020

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ASJC Scopus subject areas

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

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