![6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine structure](https://static.chemtradehub.com/structs/120/1203499-17-5-b4d1.webp "6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine structure")
6-Bromo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine
CAS Number:
1203499-17-5
Molecular Formula:
C7H7BrN2O
Chemical synthesis of quillaic acid, the aglycone of QS-21
Literature Information
Publication Date
2020-12-16
DOI
10.1039/D0QO01356K
Impact Factor
5.281
Authors
Zhi-Yong Zeng, Jin-Xi Liao, Zhen-Ni Hu, De-Yong Liu, Qing-Ju Zhang, Jian-Song Sun
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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