Patent ID: 7452999

Claim:
A process for preparing a compound of formula (VIII) comprising Step A: contacting a compound of formula (I) with a compound of the formula (II) Y—O—NH 2 (II) in a suitable solvent under conditions suitable to form a compound of the formula (III) followed by asymmetric hydrogenation Step B: contacting the compound of formula (III) with hydrogen in the presence of a chiral ligand and a catalytic amount of a hydrogenation catalyst in a suitable solvent and under conditions suitable to form a compound of the formula (IV) followed by Step C: contacting the compound of formula (IV) with a base such as a Grignard reagent in a suitable solvent under conditions suitable to form a compound of the formula (V) followed by Step D: contacting the compound of formula (V) with a compound of the formula (VI) in a suitable solvent, optionally in the presence of an activator under conditions suitable to form a compound of the formula (VII) followed by Step E: contacting the compound of formula (VII) with a formylating agent in a suitable solvent under conditions suitable to form the compound of formula (VIII): wherein X is —CH 2 —, —S—, —CH(OH)—, —CH(OR)—, —CH(SH)—, —CH(SR)—, —CF 2 —, —C═N (OR)— or —CH(F)—; Y is a hydroxyl-protecting group; R is alkyl; R 1 is aryl or heteroaryl; Ac is acetyl; each of R 2 , R 3 , and R 10 independently is hydrogen or alkyl, or (R 2 or R 3 ) collectively form a C 4 -C 7 cycloalkyl; and n is 0-3, provided that when n is 0, X is —CH 2 —.