Lignanes. 16. Premières synthèses totales du (+)-wikstromol, de la (−)-trachélogénine, de la (−)-nortrachélogénine et des lignoïdes apparentés

Resume Racemic and optically active α,β-dibenzyl-γ-butyrolactones (of synthetic origin) were hydroxylated in the α position with respect to the carbonyl group, using oxygen in the presence of LHDS. This led to (−)-trachelogenin 1 , (−)-nortrachelogenin 2 and (+)-wikstromol 3 , whose interesting pharmacological properties were recently described. These natural lignans were correlated to (±)-methyltrachelogenin 12 whose relative structure was definitely established by X-ray cristallography.