The total synthesis of (-)-nitidasin

Daniel T. Hog, Florian M.E. Huber, Peter Mayer, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

Nitidasin is a pentacyclic sesterterpenoid with a rare 5-8-6-5 carbon skeleton that was isolated from the Peruvian folk medicine " Hercampuri". It belongs to a small class of sesterterpenoids that feature an isopropyl trans-hydrindane moiety fused to a variety of other ring systems. As a first installment of our general approach toward these natural products, we report the total synthesis of the title compound. Our stereoselective, convergent route involves the addition of a complex alkenyl lithium compound to a trans-hydrindanone, followed by chemoselective epoxidation, ring-closing olefin metathesis, and redox adjustment.

Original languageEnglish (US)
Pages (from-to)8513-8517
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number32
DOIs
StatePublished - Aug 4 2014

Keywords

  • ring-closing olefin metathesis
  • sesterterpenoids
  • stereoselective synthesis
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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