Method for manufacturing prostaglandin analogue

1. A method for manufacturing a prostaglandin analogue represented by formula (I):

wherein

wherein R1 is a protecting group for hydroxy group;

wherein R2 is a protecting group for hydroxy group;

wherein R3 is a protecting group for hydroxy group, R4 and R5 are hydrogen atom, halogen atom, lower alkyl or lower alkoxy group or when R4 and R5 are lower alkyl at the same time, R4 and R5 taken together may form a cyclic group, provided that at least one of

A is

or a functional derivative thereof;

B is a single bond,

Ra is bivalent saturated or unsaturated lower-medium aliphatic hydrocarbon group, which is unsubstituted or substituted by a halogen atom, an alkyl, hydroxy, oxo, aryl or heterocyclic group, provided that one or more carbon atoms of the aliphatic hydrocarbon group may optionally be replaced with oxygen, nitrogen or sulfur atom; and Rb is hydrogen atom; saturated or unsaturated lower-medium aliphatic hydrocarbon group which may be substituted by a halogen, oxo, hydroxy, lower alkoxy, lower alkanoyloxy, cyclo(lower)alkyl, cyclo(lower)alkyloxy, aryl, aryloxy, heterocyclic or heterocyclic oxy; cyclo(lower)alkyl; cyclo(lower)alkyloxy; aryl; aryloxy; heterocyclic; or heterocyclic oxy, which comprises the step of, reacting a compound of formula (II):

wherein, X 2 is the same as X 1 except for when

Y 2 is the same as Y 1 except for when

Z 2 is the same as Z 1 except for when

provided that at least one of

and,

A, B, Ra and Rb are the same as above;

with a co-oxidizer in the presence of a tetramethylpiperidine-1-oxyl derivative;

wherein at least one of

as a result of the reacting step.

2. The method of claim 1 , wherein A is

or a functional derivative thereof.

3. The method of claim 1 , wherein the tetramethylpiperidine-1-oxyl derivative is 2, 2, 6 , 6-tetramethylpiperidine-1-oxyl.