Advertisement

Syntheses and Structural Confirmations of Members of a Heterocycle-Containing Family of Labdane Diterpenoids

Authors

  • Daniel J. Mack,

    1. Department of Chemistry and Chemical Biology, Cornell University, Baker Laboratory, Ithaca, NY 14853-1301 (USA)
    Search for more papers by this author
  • Prof. Jon T. Njardarson

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)
    • Department of Chemistry and Biochemistry, University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721 (USA)
    Search for more papers by this author

  • We thank the NSF (CHE-0848324), NIH-NIGMS (RO1 GM086584) and the University of Arizona for financial support.

Abstract

original image

Building with berries! Several labdane natural products have been synthesized for the first time by the combination of a copper-catalyzed vinyl oxirane ring expansion reaction with an abundant, inexpensive, chiral natural source (juniper berries; see scheme). These expedient (1–5 step) syntheses have resulted in the structural confirmations of five natural products and one reassignment. Reagent-controlled oxidation and 1,3-diene isomerization results are also presented.

Ancillary