SUBSTITUTED DELTA-LACTONES AND METHODS OF PREPARING SAME

摘要

The invention relates to substituted delta-lactones as well as to processes for synthesizing them, e.g., using fatty acids as starting material.

主权项

1. A method of producing a compound of formula A,wherein the is a single bond or a double bond and RA is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl; the method comprising:(i) when the compound of formula A is of formula I: reacting a compound of formula II:with ozone to obtain a compound of formula III;wherein R1 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl and R2 is H, unsubstituted or substituted C1-C20 alkyl, or unsubstituted or substituted C2-C20 alkenyl;
reacting the compound of formula III with a compound of formula IV:in the presence of a metal to produce a reaction mixture, wherein Y is halo and R3 is unsubstituted or substituted C1-C20 alkyl unsubstituted or substituted C2-C20 alkenyl, or unsubstituted or substituted aryl; and
optionally treating the reaction mixture with an acid and/or heat to obtain the compound of formula I wherein R1 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl; or alternatively,(ii) when the compound of formula A is of formula V: reacting a compound of formula VIwith ozone to obtain a compound of formula VII;wherein R5 is unsubstituted or substituted C1-C20 alkyl or unsubstituted or substituted C2-C20 alkenyl and R6 is unsubstituted or substituted C1-C10 alkyl;
reacting the compound of formula VII with a compound of formula VIII: R4—X (VIII) in the presence of a metal to produce a reaction mixture, wherein X is halo and R4 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl; and optionally treating the reaction mixture with an acid and/or heat to obtain the compound of formula V wherein R4 is unsubstituted or substituted C1-C10 alkyl, unsubstituted or substituted C3-C20 cycloalkyl, unsubstituted or substituted C2-C10 alkenyl, or unsubstituted or substituted aryl.