Total Synthesis of Marine Glycosphingolipid Vesparioside B

Journal of the American Chemical Society
Peng-Cheng GaoJin-Song Yang

Abstract

The first total synthesis of a major component of marine glycolipid vesparioside B ( Scheme 1 , 1, R1 = n-C22H45, R2 = n-C14H29) has been accomplished through a convergent [4 + 3] coupling strategy. Key steps included stereoselective installment of a set of challenging 1,2-cis-glycoside bonds. A 2-quinolinecarbonyl-assisted α-galactosylation and a novel β-arabinosylation were developed, respectively, to synthesize the α-galactofuranosidic and the β-arabinopyranosidic linkages. Furthermore, a 4,6-O-benzylidene-controlled α-galactopyranosylation reaction allowed the efficient connection of the left tetrasaccharide donor 2 with the right disaccharide lipid acceptor 3, hence leading to the total synthesis of 1.

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Citations

Aug 24, 2018·Marine Drugs·Iván Cheng-Sánchez, Francisco Sarabia
Oct 4, 2018·Chemistry : a European Journal·Sicheng Lin, Todd L Lowary
Mar 29, 2019·Angewandte Chemie·Fei YuHien M Nguyen
Jan 18, 2018·Natural Product Reports·John W BluntMichèle R Prinsep
Oct 17, 2020·The Journal of Organic Chemistry·Melanie ShadrickAlexei V Demchenko
Jun 4, 2020·The Journal of Organic Chemistry·Bo-Shun Huang, Todd L Lowary

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