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


Authors: Karimov, R. R.; Tan, D. S.; Gin, D. Y.
Article Title: Synthesis of the hexacyclic triterpene core of the jujuboside saponins via tandem Wolff rearrangement–intramolecular ketene hetero-Diels–Alder reaction
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. © 2018 Elsevier Ltd
Keywords: total synthesis; natural products; ketene hetero-diels-alder; tandem reaction; wolff rearrangement
Journal Title: Tetrahedron
Volume: 74
Issue: 26
ISSN: 0040-4020
Publisher: Elsevier Inc.  
Date Published: 2018-06-28
Start Page: 3370
End Page: 3383
Language: English
DOI: 10.1016/j.tet.2018.04.051
PROVIDER: scopus
DOI/URL:
Notes: Article -- Export Date: 2 July 2018 -- Source: Scopus
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MSK Authors
  1. Derek S Tan
    67 Tan
  2. David Y Gin
    41 Gin