Total Synthesis of Alvaradoins E and F, Uveoside, and 10-epi-Uveoside | Zendy

Kevin Ng | Zendy; Ryan Shaktah | Zendy; Laura Vardanyan | Zendy; Thomas G. Minehan | Zendy

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Total Synthesis of Alvaradoins E and F, Uveoside, and 10-epi-Uveoside

Author(s) -

Kevin Ng,

Ryan Shaktah,

Laura Vardanyan,

Thomas G. Minehan

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b03546

Subject(s) - chemistry , isothermal titration calorimetry , glycoside , titration , total synthesis , oxygen atom , fluorescence , stereochemistry , combinatorial chemistry , organic chemistry , molecule , biochemistry , physics , quantum mechanics

Concise total syntheses of the anthracenone C -glycosides alvaradoins E and F, uveoside, and 10-epi-uveoside ( 1 - 4 ) have been accomplished from chrysophanic acid 8 and bromosugar 9 . Key steps in the syntheses include the DBU-induced coupling of 8 and 9 o produce β- C -glycoside 11 , and a Pb(OAc) 4 -mediated Kochi reaction to introduce the C-1' oxygen atom of the natural products. Isothermal titration calorimetry and fluorescence binding studies reveal that compounds 1 and 2 have good affinity for the plasma protein HSA.

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