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US 2015/0087033 A1Published application
Methods for making tocoflexols and analogues thereof
AssigneesBoard of Trustees of the University of Arkansas, The United States of America as represented by the Department of Veterans Affairs
InventorsGuangrong Zheng, Cesar Compadre, Martin Hauer-Jensen, Peter Crooks, Philip Breen
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Abstract
Methods for the synthesis of tocoflexols of Formula (I) and (II) and a number of related tocol analogues are provided herein. The methods are economical and amenable to large scale production and can be performed using either pure of partially purified tocotrienols as the starting material.
Claims20
A method of making tocoflexols of Formula (I) or (II) and analogues thereof of formula (III-IX) comprising the steps of:
- (a) introducing a protective group to the phenolic hydroxyl group of a pure or partially purified tocotrienol of formula (X) to form the product of formula (XI):
- wherein R1, R2, and R3, are the same or different and are each selected from hydrogen and methyl and P is hydroxyl protective group;
- and
- (b) cleaving by oxidation the double bonds in products from step (a) in the formula (XI) to afford an aldehyde intermediate in the formula (XII):
- wherein R1, R2, R3, and P are the same as described in step (a);
- and wherein the intermediate of formula (XII) is used to produce the tocoflexols of Formula (I) or (II) or analogues thereof of formula (III-IX).
3 more elements
Dependencies are inferred from the claim text.