Synthesis of tricolorin F

The Journal of Organic Chemistry
Marco Brito-AriasClayton H. Heathcock

Abstract

A hetero-trisaccharide resin glycoside of jalapinolic acid known as tricolorin F has been synthesized. The approach involved the preparation of intermediate 5 and a subsequent coupling reaction with imidate 6 to produce disaccharide 7, which after deacetylation generated intermediate 8. A further coupling between this glycosyl acceptor and the quinovose glycosyl donor 9 resulted in the formation of the tricoloric acid C derivative 10. Basic hydrolysis afforded the intermediate 11, which was subsequently lactonized under Yamaguchi conditions to produce protected macrolactone 12. Removal of acetonide and benzyl protecting groups afforded pure tricolorin F (1).

References

Oct 24, 2001·The Journal of Organic Chemistry·Daniel P. Larson, Clayton H. Heathcock
Feb 7, 2003·Current Topics in Medicinal Chemistry·Rogelio Pereda-Miranda, Moustapha Bah

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Citations

Sep 26, 2012·Chemical Reviews·A ParentyJ-M Campagne
Aug 1, 2013·Organic Letters·San-Yong ZhuJin-Song Yang
Aug 22, 2009·Chemistry : a European Journal·Takashi NaganoAlois Fürstner
Jan 9, 2015·Journal of Asian Natural Products Research·Hong HuangLing-Li Zhang
Mar 8, 2018·Natural Product Reports·Jacob RodriguezMaciej A Walczak
Mar 5, 2019·Current Medicinal Chemistry·Kartikey Singh, Rama Pati Tripathi
Feb 21, 2009·Organic Letters·Maarten H D PostemaQunli Xu
Jul 30, 2010·The Journal of Organic Chemistry·Lin XieJin-Song Yang
Jul 10, 2014·Chemical Reviews·Juan Xie, Nicolas Bogliotti
Jun 30, 2019·Organic Letters·Jing FangQian Wan
Mar 9, 2006·Chemical Reviews·A ParentyJ-M Campagne

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