Synthesis of the hexacyclic triterpene core of the jujuboside saponins via tandem Wolff rearrangement–intramolecular ketene hetero-Diels–Alder reaction

Synthesis of the hexacyclic triterpene core of the jujuboside saponins via tandem Wolff... 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Tetrahedron Elsevier

Synthesis of the hexacyclic triterpene core of the jujuboside saponins via tandem Wolff rearrangement–intramolecular ketene hetero-Diels–Alder reaction

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Publisher
Elsevier
Copyright
Copyright © 2018 Elsevier Ltd
ISSN
0040-4020
D.O.I.
10.1016/j.tet.2018.04.051
Publisher site
See Article on Publisher Site

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.

Journal

TetrahedronElsevier

Published: Jun 28, 2018

References

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