Trichothecene degradation studies. 2. Synthesis of [13-14C]anguidine

Article abstract of DOI:10.1021/jo00380a021

An efficient degradation and resynthesis of anguidine that pivots around norketone 4 is described. The sequence from anguidine to anguidine via 4 proceeds in 12 steps with an overall yield of 30%. This work has permitted for the first time the preparation of an enantiomerically pure, high specific activity ¹⁴C-labeled epoxytrichothecene mycotoxin required for biological investigations. The radiolabel was introduced by the reaction of 4 with [¹⁴C]CH₂PPh₃.