Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement | Zendy

Takeshi Sugai | Zendy; Kengo Hanaya | Zendy; Shuhei Higashibayashi | Zendy

Open Access

Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement

Author(s) -

Takeshi Sugai,

Kengo Hanaya,

Shuhei Higashibayashi

Publication year - 2021

Publication title -

bioscience biotechnology and biochemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.509

H-Index - 116

eISSN - 1347-6947

pISSN - 0916-8451

DOI - 10.1093/bbb/zbaa021

Subject(s) - semisynthesis , chemistry , acetylation , naringenin , chalcone , oxidative phosphorylation , yield (engineering) , organic chemistry , stereochemistry , biochemistry , flavonoid , materials science , metallurgy , gene , antioxidant

Prunetin (4′,5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6′-acetoxy-2′,4″-dihydroxy-4′-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.

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