Process for making 1,3-dioxane derivatives

Details Process for making 1,3-dioxane derivatives Process for making 1,3-dioxane derivatives

1987-10-27

1990-02-13

Shine, W. J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549375, C07D31906

Patent

active

049008463

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)alkanesulphonamideo, 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 thereapeutic agents.

REFERENCES:
patent: 4567197 (1986-01-01), Brewster et al.
Bull. Soc. Chim., Japan, 1968, 41, 1468-1471.
Impotoc Search report of EP94239-1/86.
Lewis et al; Tetrahedron, vol. 23, pp. 4197-4208; 3-Hydroxymethyl-4-Aryl-4-Hydroxybutanoic Acid Lactones.
Lawlor et al; Tetrahedron, vol. 24, No. 21, pp. 2211-2213, 1983; A Convenient Synthesis of 4-Substituted Paraconic Acids.

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