Journal
ACS OMEGA
Volume 5, Issue 19, Pages 11043-11057Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.0c00932
Keywords
-
Categories
Funding
- National Eye Institute [R01EY025641]
- BrightFocus Foundation [M2015301]
- National Research Foundation - Korean government, MSIP [NRF-2014M3C1A3054139, NRF-2017M3A9C8027781]
- Korea Health Technology R&D Project through the Korea Health Industry Development Institute (KHIDI) - Ministry of Health Welfare [HI14C1135]
- National Research Foundation of Korea [2014M3C1A3054139, 2017M3A9C8027781] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
Ask authors/readers for more resources
Homoisoflavonoids are in the subclass of the larger family of flavonoids but have one more alkyl carbon than flavonoids. Among them, 5,7,8-trioxygenated homoisoflavonoids have not been extensively studied for synthesis and biological evaluation. Our current objective is to synthesize 2 5,7,8-trioxygenated chroman-4-ones and 12 5,7,8-trioxygenated homoisoflavonoids that have been isolated from the plants Bellevalia eigii, Drimiopsis maculata, Ledebouria graminifolia, Eucomis autumnalis, Eucomis punctata, Eucomis pallidiflora, Chionodoxa luciliae, Muscari comosum, and Dracaena cochinchinensis. For this purpose, 1,3,4,5-tetramethoxybenzene and 4'-benzyloxy-2',3'-dimethoxy-6'-hydroxyacetophenone were used as starting materials. Asymmetric transfer hydrogenation using Noyori's Ru catalyst provided 5,7,8-trioxygenated-3-benzyichroman-4-ones with R-configuration in high yield and enantiomeric excess. By selective deprotection of homoisoflavonoids using BCl3, the total synthesis of natural products including 10 first syntheses and three asymmetric syntheses has been completed, and three isomers of the reported dracaeconolide B could be provided. Our research on 5,7,8-trioxygenated homoisoflavonoids would be useful for the synthesis of related natural products and pharmacological applications.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available