An enantiospecific synthesis of jiadifenolide

David A. Siler, Jeffrey D. Mighion, Erik J. Sorensen

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

Abstract

A Robinson annulation, van Leusen homologation, and a desymmetrizing C-H oxidation enabled an enantiospecific synthesis of the neurotrophic natural product jiadifenolide. From a pulegone-derived building block, a key propellane intermediate was constructed through the use of simple reagents in a highly diastereoselective fashion. A short series of oxidations of this tricylic framework allowed progression to the natural product. Establishing the framework: A Robinson annulation, van Leusen homologation, and a desymmetrizing C-H oxidation enabled an enantiospecific synthesis of the neurotrophic natural product jiadifenolide. From a pulegone-derived building block, a key propellane intermediate was constructed through the use of simple reagents in a highly diastereoselective fashion. A short series of oxidations of this tricylic framework allowed progression to the natural product.

Original languageEnglish (US)
Pages (from-to)5332-5335
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number21
DOIs
StatePublished - May 19 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • C-H activation
  • chiral pool
  • natural products
  • terpenoids
  • total synthesis

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