Determination of the stereochemistry of (-)-koninginin A by an X-ray analysis of its synthetic sample.
The absolute configuration of (-)-koninginin A [10-hexyl-11, 12-dioxatricyclo[7.2. 1.0<1 ,6>]dodecane-2,5-diol (1)], the antibiotic metabolite of Trichoderma koningii and T. harzianum, was determined as 1S, 2R, 5S, 6S, 9S, 10S by an X-ray crystallographic analysis of its synthetic sample coupled with the established stereochemical outcome of Sharpless asymmetric dihydroxylation used as the key reaction to prepare intermediate 4.
D001584:Benzoxepins / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism; D014242:Trichoderma / Q000737:chemistry
D001584:Benzoxepins; D006575:Heterocyclic Compounds, 3-Ring; C472987:koninginin A