Charles Frederick Howell

The synthesis of heterocyclic C-terminal units which mimic the transition state in the cleavage of the Leu-Val bond of angiotensinogen by renin

The stereospecific synthesis of (S)2-amino-3-cyclohexyl-(R)1-(2- furanyl)-propan-1-ol (17) and (S) 2-amino-3-cyclohexyl-(R)1-(2-thienyl)-propan-1-ol (18) from t-Boc-L-phenylalanine is described. Reduction of the furan ring of (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2-oxazolidinone (15) gave two tetrahydrofuranyl diastereomers (21) and (22). Each tetrahydrofuranyl oxazolidinone (21 and 22) was converted stereospecifically in high yield to the (S, R, R) and the (S, R, S) tetrahydrothienyl oxazolidinones (29) and (27), respectively