Chemoenzymatic synthesis of enantiomers of a new retinoid to investigate the role of chirality in the biological response

We have prepared both enantiomers of a new retinoid (IIa and IIb) partly by using lipase resolution of 1-acetoxy-1-(5, 6, 7, 8 - tetrahydro - 5, 5, 8, 8-tetramethyl-2-naphthyl) ethane. Absolute configuration of resulting secondary carbinols (4a and 4b) was assigned using lanthanide induced shifts NMR experiments on MTPA esters of 4a and 4b. Only the enantiomer (R-(−)-IIa) is active on the differentiation of F9 embryonal teratocarcinoma cells (F9 cells).