First total synthesis and determination of the absolute configuration of the stress factor (+)-hydroxymyoporone

The first total synthesis of the stress factor (+)-hydroxymyoporone (4) is presented. The key step is an asymmetric allylation of the methyl ketone 10 which proceeds with excellent selectivity and yield. In addition, it was p roven that the allylation assignment of the absolute configuration of hydro xymyoporone published in the natural literature is incorrect; the correct s tructure of the (+)-enantiomer is depicted in the structural formula 4.