Semisynthesis of (+)- and (-)-goniomitine from (-)- and (+)-vincadifformine

The first biomimetic semisynthesis of goniomitine has been accomplished in nine steps with 11% overall yield starting from vincadifformine. Natural (-)- and unnatural (+)-goniomitine were prepared from (+)- and (-)-vincadifformine, respectively. The evaluation of the antiproliferative effect of both enantiomers proved unnatural (+)-goniomitine to be more potent, but this enantiomer as well as some close derivatives displayed a moderate activity only. (c) 2012 Published by Elsevier Ltd.