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).
Original language | English |
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Pages (from-to) | 4567-4570 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 69 |
Issue number | 14 |
DOIs | |
State | Published - 9 Jul 2004 |