Process for the production of a cyclopentenol derivative

Details Process for the production of a cyclopentenol derivative Process for the production of a cyclopentenol derivative

C - Chemistry, Metallurgy

07

C

C07C 35/06 (2006.01) C07B 37/00 (2006.01) C07C 29/10 (2006.01) C07C 29/32 (2006.01) C07C 43/188 (2006.01) C07D 307/20 (2006.01) C07D 309/12 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2122768

ABSTRACT A process for the production of a cyclopentenol compound represented by the formula I: Image wherein R1 represents a 2-propenyl group or a 2-propynyl group, which comprises the steps of; (i) protecting the hydroxyl group of the cyclopentenolone compound II: Image II wherein R1 is the same as defined above to give a cyclopentenolone derivative represented by the formula III: Image III wherein R1 is the same as defined above and A is a protecting group for a hydroxyl group; (ii) reacting a mixture of zinc and dibromomethane or diiodomethane in an inert organic solvent with titanium tetrachloride; (iii) reacting the resulting reaction mixture with a cyclopentenolone derivative III to give a cyclopentenol derivative IV: IV Image wherein R1 and A are the same as defined above; and (iv) removing the protecting group A from the cyclopentenol derivative represented by the formula IV to give the cyclopentenol compound I.

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