A Short and Convenient Chemical Route to Optically Pure 2-Methyl Chromanmethanols. Total Asymmetric Synthesis of β-, γ-, and δ-Tocotrienols
Document Type
Article
Publication Date
8-31-2007
Description
(Chemical Equation Presented) With use of inexpensive commercially available raw materials, chromanmethanol precursors to the natural β-, γ-, and δ-tocotrienols have been prepared in high yield. Enzymatic resolution afforded chiral chromanmethanols in high enantiomeric excess. Subsequent attachment of the farnesyl side chain was high yielding, thus allowing the preparation of asymmetric β-, γ-, and δ-tocotrienols in one final step wherein simultaneous deprotection of the phenol and removal of the sulfone group occurs. This chemistry provides the first synthesis of natural-series β-tocotrienol.
Citation Information
Couladouros, Elias A.; Moutsos, Vassilios I.; Lampropoulou, Maria; Little, James L.; and Hyatt, John A.. 2007. A Short and Convenient Chemical Route to Optically Pure 2-Methyl Chromanmethanols. Total Asymmetric Synthesis of β-, γ-, and δ-Tocotrienols. Journal of Organic Chemistry. Vol.72(18). 6735-6741. https://doi.org/10.1021/jo0705418 PMID: 17685653 ISSN: 0022-3263