Synthesis of tricolorin F.
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).
Brito-Arias
Marco
M
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Pereda-Miranda
Rogelio
R
Heathcock
Clayton H
CH
D027722:Convolvulaceae / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006868:Hydrolysis; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
D006027:Glycosides; C488417:tricolorin F