Patent ID: 8669365

Claim:
A process for preparing a compound of formula 136: wherein Y is CR 7 R 8 ; R 1 is H, alkyl, amino, hydroxyl, carboxyl, carbamoyl, alkoxy, hydroxyl, sugar or a protected hydroxyl group; R 2 is H, alkyl, alkenyl, alkynyl, nitrile, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, or heteroaralkyl; or R 1 and R 2 taken together form ═O, ═S, ═N(OR 9 ), ═N(R 9 ), ═C(R 9 ) 2 , or ═N(N(R 9 ) 2 ); each of R 3 , R 4 , and R 5 is, independently, H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, or heteroaralkyl; or R 3 and R 4 or R 4 and R 5 taken together form a bond; R 6 is H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, heteroaralkyl, haloalkyl, —OR 9 , —C(O)R 9 , —CO 2 R 9 , —SO 2 R 9 , —C(O)N(R 9 )(R 9 ), —[C(R 9 ) 2 ] q R 9 , —[(W)—N(R 9 )C(O)] q R 9 , —[(W)—C(O)] q R 9 , —[(W)—C(O)O] q R 9 , —[(W)—OC(O)] q R 9 , —[(W)—SO 2 ] q R 9 , —[(W)—N(R 9 )SO 2 ] q R 9 , —[(W)—C(O)N(R 9 )] q R 9 , —[(W)—O] q R 9 , —[(W)—N(R 9 )] q R 9 , —[(W)—S] q R 9 , or a nitrogen protecting group; wherein each W independently for each occurrence is a diradical; each q is independently 1, 2, 3, 4, 5, or 6; each of R 7 and R 8 is, independently, H, alkyl, amido, halide, or ester; and each R 9 is, independently, H, alkyl, alkenyl, alkynyl, aryl, cycloalkyl, heterocycloalkyl, aralkyl, heteroaryl, or heteroaralkyl; said process comprising the step of: contacting a compound of formula 136a with a haloalkylzinc phosphate cyclopropanating agent; wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 are as defined above; to form said compound of formula 136; wherein said haloalkylzinc phosphate cyclopropanating agent is formed by combining a phosphoric acid of formula 141a or salt thereof, a dialkylzinc, and a dihaloalkylane of formula 141b: wherein each of X and X′ is independently chloride, bromide, or iodide; each of R 7 and R 8 is independently H, alkyl, halide, amido, or ester; and each of R 10 and R 11 is independently alkyl, alkenyl, aralkyl, aryl, heteroaryl, or heteroaralkyl.