Patent ID: 8350059

Claim:
A method for making a compound of formula (V): wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 3-6 unconjugated alkenyl and C 3-6 unconjugated alkynyl; R 3 is selected from the group consisting of hydrogen and a base stable oxygen protecting group; R 5 and R 6 are each independently selected from the group consisting of hydrogen, halogen, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 1-6 alkoxy, phenyl and benzyl, wherein the phenyl or benzyl are substituted with 0, 1, 2, or 3 substituents independently selected from halogen, hydroxyl, C 1-3 alkyl, and NH 2 ; or R 5 and R 6 are taken together with the carbons on which they are attached to form a 5-6 membered unconjugated carbocyclic ring; R 11 and R 12 are each independently selected from the group consisting of hydrogen and a base stable oxygen protecting group; or R 11 and R 12 are taken together to form a 5 membered heterocyclyldiyl of structure (a): wherein R 19 and R 20 are each independently selected from the group consisting of hydrogen, C 1-6 alkyl, C 1-6 haloalkyl, C 1-6 alkoxy and phenyl, or R 19 and R 20 together represent a fluorenyl moiety of structure (b): R 13 is selected from the group consisting of hydrogen and a base stable oxygen protecting group; comprising reacting a compound of formula (I): wherein R 4 is hydrogen; with a compound of formula (II): wherein X is a halogen; under suitable basic conditions, comprising (i) converting the primary alcohol (I) into the corresponding aldehyde, (ii) converting the phosphonium ion (II) into the corresponding ylide, and (iii) reacting the aldehyde and the ylide, such that a compound of formula (V) is formed.