Patent ID: 7371865

Claim:
A process for the manufacture of an enantiomerically pure form or a racemic form of a compound of formula or a salt thereof, or a lactone thereof, wherein the element represents —CH═CH—, and R represents the cyclic residue of formula comprising (a) reacting a compound of formula (III a) or (III b) wherein X 4 and X 5 , independently of one another, represents C 1 -C 7 -alkyl or phenyl-C 1 -C 7 -alkyl; X 6 , X 7 , and X 8 , independently of one another, represent phenyl that is unsubstituted or substituted by one or more substituents selected from the group consisting of C 1 -C 7 alkyl, hydroxy, C 1 -C 7 alkoxy, C 2 -C 8 alkanoyl-oxy, halogen, nitro, cyano, and CF 3 ; and Hal − represents a halide anion; with a metallated alkane to form the corresponding ylide and then reacting the resulting ylide intermediate with a compound of formula wherein X represents etherified hydroxy, esterified hydroxy, or unsubstituted or mono- or di-substituted amino; X 1 is protected hydroxy; X 2 represents C 1 -C 7 alkyl; and X 3 represents hydrogen or one or more substituents selected from the group consisting of C 1 -C 7 alkyl, hydroxy, C 1 -C 7 alkoxy, C 2 -C 8 alkanoyl-oxy, halogen, nitro, cyano, and CF 3 , resulting in a compound of formula (III d) wherein X 1 , X 2 and X 3 have the meanings as defined above, Y represents a group of formula (X 4 O)(X 5 O)P(═O)— or (X 6 )(X 7 )(X 8 )P + Hal − , and X 4 , X 5 , X 6 , X 7 , X 8 and Hal − have the meanings as defined above; (c) reacting a compound of formula (III d) with an aldehyde of formula (III f) R—CH(═O) resulting in a compound of formula (III g′) wherein R, X 1 , X 2 , X 3 and the element have the meanings as defined above; (e) converting a compound of formula (III g′), to a compound of formula (III i) by removing the hydroxy protection group; wherein R, X 2 , X 3 and the element have the meanings as defined above; and subsequent reduction of said compound of formula (III i) to a compound of formula (III h) wherein R, X 2 , X 3 and the element have the meanings as defined above; (f) hydrolyzing a compound of formula (III h) to a compound of formula (I) or a salt thereof; (g) isolating a resulting compound of formula (I) or a salt thereof.