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ChemInform Abstract: Nucleosides and Nucleotides. Part 190. The First Synthesis of Herbicidin B. Stereoselective Construction of the Tricyclic Undecose Moiety by a Conformational Restriction Strategy Using Steric Repulsion Between Adjacent Bulky Silyl Protecting Groups on a Pyranose Ring.
First published: 10 June 2010
Abstract
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ChemInform Abstract
Key step in the first total synthesis of antibiotic herbicidin B (I) is the novel regioselective aldol-type C-glycosidation reaction of methyl 3,4-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl) -1-phenylthio-2-ulos-β-D-glucuronate promoted by samarium diiodide to give the corresponding 1-enolate.
