Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue -, Pages -Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.11.135
Keywords
Claisen-Cope rearrangement; flavonol; icariin; prenylation; regioselectivity
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Funding
- National Natural Science Foundation of China [21172214]
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The hemisynthesis of the naturally occurring bioactive flavonoid glycoside icariin (1) has been accomplished in eleven steps with 7% overall yield from kaempferol. The 4'-OH methylation of kaempferol, the 8-prenylation of 3-O-methoxymethyl-4'-O-methyl-5-O-prenyl-7-O-benzylkaempferol (8) via para-Claisen-Cope rearrangement catalyzed by Eu(fod)(3) in the presence of NaHCO3, and the glycosylation of icaritin (3) are the key steps.
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