Synthesis of the hexacyclic triterpene core of the jujuboside saponins via tandem Wolff rearrangement-intramolecular ketene hetero-Diels-Alder reaction. Academic Article uri icon

Overview

abstract

  • The jujubosides are saponin natural products reported to have immunoadjuvant, anticancer, antibacterial, antifungal, and antisweet activities. The triterpene component, jujubogenin contains a unique tricyclic ketal motif comprising the DEF ring system. Herein, we describe our efforts toward the total synthesis of jujubogenin, using a sterically-demanding intermolecular Diels-Alder reaction to assemble the C-ring and a tandem Wolff rearrangement-intramolecular ketene hetero-Diels-Alder reaction to form the DF-ring system. Acid-catalyzed cyclization of the resulting bicyclic enol ether then closes the E-ring to provide the hexacyclic core of jujubogenin.

publication date

  • April 19, 2018

Identity

PubMed Central ID

  • PMC6242285

Scopus Document Identifier

  • 85046758445

Digital Object Identifier (DOI)

  • 10.1016/j.tet.2018.04.051

PubMed ID

  • 30467444

Additional Document Info

volume

  • 74

issue

  • 26