A process for preparing an epoxide-containing azaepothilone of formula VII wherein R A is selected from the group consisting of substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl, R B is selected from the group consisting of H, alkyl, and substituted or unsubstituted aryl, R C is selected from the group consisting of H, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and fluoroalkyl, wherein substituted aryl or heteroaryl moieties at positions RA, RB, and RC are substituted with one or more groups selected from halo, hydroxyl, amino, alkylamino, amido, acyl, nitro, cyano, and alkoxy; the process comprising: a) contacting a bornane derivative of a compound of formula II wherein Z is selected from the group consisting of and R 1 and R 2 are independently selected from the group consisting of hydrogen, triethylsilyl, triisopropylsilyl (TIPS), tert-butyldimethylsilyl and tert-butyldipehnylsilyl (TBDPS), with a vinyl halide of formula III wherein X is a halogen selected from the group consisting of Cl, Br, and I, or a non-halogen selected from the group consisting of triflate and phosphate, and R 3 and R 4 are independently selected from the group consisting of H, tert -butyloxycarbonyl, and tert- butylsulfonyl (SO 2 t -Bu), or together R 3 and R 4 are CPh 2, in the presence of a transition metal catalyst to provide a compound of the formula IV and b) converting the compound of formula IV to a compound of formula V by converting Z to OH and converting R 3 and R 4 to H when one or both of R 3 and R 4 are other than H, wherein the converting steps are conducted in any order; and c) cyclizing the compound of formula V to the compound of formula VI. d) treating a compound of formula VI with an epoxidizing agent to form a compound of formula VIII and e) deprotecting the compound of formula VIII to provide the epoxide containing azaepothilone VII. wherein R A is selected from the group consisting of substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl, R B is selected from the group consisting of H, alkyl, and substituted or unsubstituted aryl, R C is selected from the group consisting of H, alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and fluoroalkyl, a) contacting a bornane derivative of a compound of formula II wherein Z is selected from the group consisting of and R 1 and R 2 are independently selected from the group consisting of hydrogen, triethylsilyl, triisopropylsilyl (TIPS), tert-butyldimethylsilyl and tert-butyldipehnylsilyl (TBDPS), with a vinyl halide of formula III wherein X is a halogen selected from the group consisting of Cl, Br, and I, or a non-halogen selected from the group consisting of triflate and phosphate, and R 3 and R 4 are independently selected from the group consisting of H, tert -butyloxycarbonyl, and tert- butylsulfonyl (SO 2 t -Bu), or together R 3 and R 4 are CPh 2, in the presence of a transition metal catalyst to provide a compound of the formula IV and b) converting the compound of formula IV to a compound of formula V by converting Z to OH and converting R 3 and R 4 to H when one or both of R 3 and R 4 are other than H, wherein the converting steps are conducted in any order; and c) cyclizing the compound of formula V to the compound of formula VI. d) treating a compound of formula VI with an epoxidizing agent to form a compound of formula VIII and e) deprotecting the compound of formula VIII to provide the epoxide containing azaepothilone VII.