Process for making 1,3-dioxane derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acids and salts thereof

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564 99, 549373, 549375, C07C 5948, C07C14372

Patent

active

047230371

ABSTRACT:
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 cyclized to the required dioxane derivative of formula I. The invention also provides a novel process for making the aldehydes of formula II 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.

REFERENCES:
patent: 4567197 (1986-01-01), Brewster
Bull. Soc. Chim. Japan, 1968, 41, 1468-1471, Takeda et al.
Impadoc Search Report of EP 94239-1/86.

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