The total synthesis of (-)-nitidasin

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

Research output: Contribution to journalArticle

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

Fingerprint

Lithium Compounds
Lithium compounds
Epoxidation
Alkenes
Biological Products
Olefins
Medicine
Carbon
Oxidation-Reduction
hydrindane

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Hog, D. T., Huber, F. M. E., Mayer, P., & Trauner, D. (2014). The total synthesis of (-)-nitidasin. Angewandte Chemie - International Edition, 53(32), 8513-8517. https://doi.org/10.1002/anie.201403605

The total synthesis of (-)-nitidasin. / Hog, Daniel T.; Huber, Florian M.E.; Mayer, Peter; Trauner, Dirk.

In: Angewandte Chemie - International Edition, Vol. 53, No. 32, 04.08.2014, p. 8513-8517.

Research output: Contribution to journalArticle

Hog, DT, Huber, FME, Mayer, P & Trauner, D 2014, 'The total synthesis of (-)-nitidasin', Angewandte Chemie - International Edition, vol. 53, no. 32, pp. 8513-8517. https://doi.org/10.1002/anie.201403605
Hog, Daniel T. ; Huber, Florian M.E. ; Mayer, Peter ; Trauner, Dirk. / The total synthesis of (-)-nitidasin. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 32. pp. 8513-8517.
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