Scalable Synthesis of Quillaic Acid from Oleanolic Acid and Divergent Synthesis of Analogues Thereof
Xin-Xin Yang , Jia-Jia Wang , Xian-Yu Zhou , Yang Hu , Jin-Xi Liao , Hui Liu , Jian-Song Sun
Chinese Journal of Chemistry ›› 2026, Vol. 44 ›› Issue (9) : 1373 -1378.
QS-21 is one of the most potent saponin immunoadjuvants. However, its wide applications in subunit vaccine development are seriously restricted by its limited availability. Among the factors causing the scarcity of QS-21, the difficult acquisition of quillaic acid (QA) on large scale is the fundamental one. Based on two steps of C–H functionalization, the Sanford C–H acetoxylation and the Yu modified Schonecker-Baran C–H oxidation, scalable (gram-scale) and concise (20 steps) synthesis of QA from oleanolic acid (OA) was accomplished. Moreover, based on the versatile 23,24-Me-diacetoxylized side product, the divergent synthesis of QA derivatives, including hederagenin analogues, oxetane-containing OA, as well as 24-Me-nor-OA, was conveniently accomplished.
Triterpene / Quillaic acid / Oleanolic acid / Immunoadjuvant / QS-21 / Scalable synthesis / Divergent synthesis / C–H oxidation
2026 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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