Sirtuin activating compounds and processes for making the same

摘要

The present invention includes methods for preparing resveratrol, resveratrol esters and substituted and unsubstituted stilbenes of the formula given below; where each Y is —O or halogen, each Z is —O or halogen, each n and each m is independently the value of 0, 1, 2, 3, 4 or 5, each A and each B is independently selected from Pn, R or absent, each V and each W is independently selected from Pn, straight or branched alkyl of from 2 to 6 carbon atoms and cycloalkyl of from 3 to 8 carbon atoms, alkoxy, phenyl, benzyl or halogen, R is independently selected from the group comprising alkyl with at least one carbon atom, aryl and aralkyl, Pn is an alcohol protecting group and diastereoisomers of the foregoing. The compounds are made from a multi-step process including a N-heterocyclic carbene-type ligand coupling in the presence of a base with benzyol halide and styrene coupling partners. These compounds show increased stability for use in the food, cosmetic and pharmaceutical industries.;

主权项

1. A process for preparing a compound of Formula I wherein each Y and each Z when present is independently selected from: —O, —O(C═O), —(C═O)—O, —O—(C═O)—O, —O—(C═O)—NH, —O—(C═O)—NR, —NH—(C═O)—O, —NR—(C═O)—O, —NH—(C═O), —NR—(C═O), —(C═O)—NH, —(C═O)—NR, —NH, —NR, N-containing heterocylic ring, —S, and halogen; each n and each m is independently the value of: 0, 1, 2, 3, 4, or 5; each A and each B when present is independently selected from: H and R, wherein when any Y or Z is —O, then A and B may also be selected from R, H, and P; V and W are H; each R when present is independently selected from: alkyl, aryl, and aralkyl; each P when present is an alcohol protecting group; and pharmaceutically and cosmetically acceptable salts thereof and diastereoisomers of the foregoing; comprising the step of coupling a benzoyl halide compound of Formula IC wherein X is halogen, with a 4-substituted styrene compound of Formula IE with a transition metal catalyst, N-heterocyclic carbene-type ligand and a first base.