Assembly of Terpenoid Cores by a Simple, Tunable Strategy

Ouidad Lahtigui, Fabien Emmetiere, Wei Zhang, Liban Jirmo, Samira Toledo-Roy, John C. Hershberger, Jocelyn M. Macho, Alexander J. Grenning

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Oxygenated, polycyclic terpenoid natural products have important biological activities. Although total synthesis of such terpenes is widely studied, synthetic strategies that allow for controlled placement of oxygen atoms and other functionality remains a challenge. Herein, we present a simple, scalable, and tunable synthetic strategy to assemble terpenoid-like polycycloalkanes from cycloalkanones, malononitrile, and allylic electrophiles, abundantly available reagent classes.

Original languageEnglish (US)
Pages (from-to)15792-15796
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number51
DOIs
StatePublished - Dec 19 2016
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • allylic alkylation
  • deconjugative alkylation
  • Knoevenagel adducts
  • terpene synthesis
  • [3,3] Cope rearrangement

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