Determination of the Stereochemistry of (−)-Koninginin A by an X-ray Analysis of Its Synthetic Sample

Abstract

  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.