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Determination of the stereochemistry of (-)-koninginin A by an X-ray analysis of its synthetic sample.

Kenji K Mori, Masahiko M Bando, and Kaoru K Abe

Biosci Biotechnol Biochem 66(8):1779-81 (2002) PMID 12353648

The absolute configuration of (-)-koninginin A [10-hexyl-11, 12-dioxatricyclo[7.2. 1.01 ,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.

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