Process for making 1,3-dioxane derivatives

C - Chemistry – Metallurgy – 07 – D

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260/351.1

C07D 319/06 (2006.01) C07C 45/59 (2006.01) C07C 47/27 (2006.01) C07C 47/273 (2006.01) C07C 47/277 (2006.01) C07C 59/64 (2006.01) C07D 307/20 (2006.01) C07D 307/33 (2006.01) C07D 319/08 (2006.01)

Patent

CA 1283926

A B S T R A C T PROCESS FOR MAKING 1,3-DIOXANE DERIVATIVES The invention provides a novel process for making novel (4-phenyl-1,3-dioxan-cis-5-yl)alkenoic acids of the formula I in which Ra and Rb are independently hydrogen, alkenyl, alkyl, halogenoalkyl, pentafluorophenyl, aryl or aryl-(1-4C)alkyl; or Ra and Rb together are polymethylene; Rc is hydroxy or (1-6C)alkanesulphonamido, A is vinylene, n is 1, Y is polymethylene, and benzene ring B bears various optional substituents. The process involves the reaction of an aldehyde of formula II with an ylid to give an erythro-diol of formula III which is then cyclised to the required dioxane derivative of formula I. The invention also provides a novel process for making the aldehydes of formula XI from the corresponding lactols of formula IIa, which are themselves obtained with the correct trans-stereochemistry by two selective reductions of a trans-phenylparaconic acid of formula V. The compounds of formula I are useful as therapeutic agents.

467020

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