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Updated: Jun 8, 2026
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Studies toward the total syntheses of cucurbitacins B and D
Michael E Jung1, Rebecca M Lui
1Department of Chemistry, Biochemistry, University of California, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu
Abstract:
Synthetic efforts toward the convergent construction of the tetracyclic triterpenoids cucurbitacins B and D are described. The results of a Diels-Alder study examining the effects of steric and electronic variations of 2-methyl-2-cyclohexenone on the endo/exo-diastereoselectivity of the reaction are presented. The diastereomer of the core of the cucurbitacins, epimeric at C8, C9, and C10, 51, was synthesized via a highly regio- and stereoselective Diels-Alder reaction of the diene 4 and the novel dienophile 50.
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