Issue 4, 2021

Chemical synthesis of quillaic acid, the aglycone of QS-21

Abstract

With the easily available protoescigenin as a starting material, a protocol to chemically synthesize quillaic acid was established. Benefiting from the scalability of each step comprising the novel protocol, the route featured robustness. Moreover, the devised protocol also exhibited outstanding flexibility, and other scarce and difficult-to-access oleanane-type aglycones, such as echinocystic acid, acacic acid lactone, as well as analogues derived from the D/E-ring rearrangement, C16,21 intramolecular etherification, and E-ring modification with C-substituents, could be conveniently accessed by sharing the common intermediates with quillaic acid.

Graphical abstract: Chemical synthesis of quillaic acid, the aglycone of QS-21

Supplementary files

Article information

Article type
Research Article
Submitted
01 Nov 2020
Accepted
16 Dec 2020
First published
16 Dec 2020

Org. Chem. Front., 2021,8, 748-753

Chemical synthesis of quillaic acid, the aglycone of QS-21

Z. Zeng, J. Liao, Z. Hu, D. Liu, Q. Zhang and J. Sun, Org. Chem. Front., 2021, 8, 748 DOI: 10.1039/D0QO01356K

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