Total synthesis of two isoflavone C-glycosides: genistein and orobol 8-C-beta-D-glucopyranosides

Carbohydrate Research
Shingo SatoOnodera Jun-ichi

Abstract

Genistein and orobol 8-C-beta-D-glucopyranosides (1 and 3) were firstly synthesized in overall yields of 39% and 41% from 2,4-di-O-benzylphloroacetophenone (4), as follows: (1) the formation of the chalcone (6, 7) by aldol condensation of the benzyl-protected C-glycosylphloroacetophenone (5), a key intermediate of the total synthesis of 1 and 3 and synthesized by a C-glycosylation method involving the O-->C glycoside rearrangement of 4 in 96% yield; (2) the formation of isoflavones (10, 11 and 12, 13) by the formation of acetals by oxidative rearrangement of the protected chalcones (8 and 9) using Tl(NO3)3, followed by acid-catalyzed cyclization; (3) a final debenzylation by hydrogenolysis.

References

Sep 25, 2002·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Sabine E KullingManfred Metzler

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Citations

Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Johannes H van TonderJ Marthinus Janse van Rensburg
Jul 15, 2011·Acta Crystallographica. Section E, Structure Reports Online·Mukut GohainBarend C B Bezuidenhoudt
Mar 8, 2011·Applied and Environmental Microbiology·K H M Nazmul Hussain NazirHiroyuki Wariishi
Jul 3, 2013·Chemical & Pharmaceutical Bulletin·Kazufumi MisawaShingo Sato
Apr 12, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Djamila MerianeSabrina Boutefnouchet
Oct 8, 2016·Organic & Biomolecular Chemistry·Xiong WeiZhongjun Li
Sep 16, 2017·Chemical Reviews·You Yang, Biao Yu
Dec 28, 2017·Chemical Reviews·Kei KitamuraKeisuke Suzuki
Nov 9, 2019·Journal of Natural Products·Phaladi KunyaneMamoalosi A Selepe

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