Regioselective Synthesis of 6‐Prenylpolyhydroxyisoflavone (Wighteone) and Wighteone Hydrate with Hypervalent Iodine

Hossain, Mohammad Mamun; Tokuoka, Takanori; Yamashita, Kazuyo; Kawamura, Yasuhiko; Tsukayama, Masao

doi:10.1080/00397910500514121

Cited by 18 publications

(1 citation statement)

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“…Isoflavones possess a 3-aryl flavone structure 8 and are biosynthetically derived from flavanones 7 through an oxidative rearrangement catalyzed by the cytochrome P450 enzyme isoflavone synthase (IFS). − Intrigued by this biosynthetic relationship and encouraged by literature precedence for the total synthesis of isoflavonoids from flavanones or chalcones via Tl(III)- − or hypervalent iodine-mediated ,− oxidative 1,2-aryl migration, we decided to investigate the potential of this reaction for the total synthesis of prenylated isoflavones. At the outset of this project we undertook a comprehensive survey of the literature examples for flavanone to isoflavone oxidative rearrangements (reaction 7 → 8 in Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Scope and Applications of 2,3-Oxidative Aryl Rearrangements for the Synthesis of Isoflavone Natural Products

2021

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The reaction of flavanones with hypervalent iodine reagents was investigated with a view to the synthesis of naturally occurring isoflavones. In contrast to several previous reports in the literature, we did not observe the formation of any benzofurans via a ring contraction pathway, but could isolate only isoflavones, resulting from an oxidative 2,3aryl rearrangement, and flavones, resulting from an oxidation of the flavanones. Although the 2,3-oxidative rearrangement allows a synthetically useful approach toward some isoflavone natural products due to the convenient accessibility of the required starting materials, the overall synthetic utility and generality of the reaction appear to be more limited than previous literature reports suggest.

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