TOTAL SYNTHESES OF (-)-TRACHELOGENIN, (-)-NORTRACHELOGENIN AND (+)-WIKSTROMOL

Article abstract of DOI:10.1016/S0040-4039(00)99653-9

The title compounds were obtained by α-hydroxylation of the corresponding α,β-dibenzyl-γ-butyrolactones (lignans of synthetic origin), and were correlated to (+/-)-methyltrachelogenin 9 whose relative structure was definitely established by X-ray cristallography. (-)-Trachelogenin 1 and (-)-nortrachelogenin 12 thus have the (8S,8'S) absolute configuration, whereas (+)-nortrachelogenin 20 (or wikstromol) has the (8R,8'R) absolute configuration.