Atropo-anantioselective synthesis of a simplified analog of mastigophorenes A and B

Article abstract of DOI:10.1016/S0040-4020(97)10362-3

A first approach to the atroposelective total synthesis of mastigophorenes is described, the directed preparation of a structurally slightly modified analog of mastigophorenes A and B, with a tert-butyl instead of a substituted, chiral cyclopentyl residue. Its (partially protected) monomeric half is dimerized by oxidative (phenolic) coupling to give the corresponding biphenyl in a racemic form, or atropo-enantioselectively via the corresponding biaryl lactone, to give the M- or, optionally, the P-enantiomeric form, by stereoselective ring opening and subsequent standard transformations.