Total synthesis of buergerinin F and buergerinin G.
Syntheses of buergerinin F (1) and buergerinin G (2) were carried out to establish the absolute stereochemistry of these natural products. A linear sequence was used to synthesize 1 in 15 steps and 9% overall yield from thymidine. Subsequent oxidation of 1 with ruthenium tetroxide afforded 2 in 77% yield.
Department of Chemistry, The Ohio State University, Columbus 43210, USA.
Jeong-Seok
JS
Han
Todd L
TL
Lowary
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D006575:Heterocyclic Compounds, 3-Ring / Q000032:analysis / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*; D032266:Scrophularia / Q000737:chemistry*; D013237:Stereoisomerism; D013936:Thymidine / Q000737:chemistry
D006575:Heterocyclic Compounds, 3-Ring; C479621:buergerinin F; C479622:buergerinin G; D013936:Thymidine