A short and convenient chemical route to optically pure 2-methyl chromanmethanols. Total asymmetric synthesis of beta-, gamma-, and delta-tocotrienols.
With use of inexpensive commercially available raw materials, chromanmethanol precursors to the natural beta-, gamma-, and delta-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 beta-, gamma-, and delta-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 beta-tocotrienol.
Couladouros
Elias A
EA
Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, GR 118 55 Athens, Greece. ecoula@chem.demokritos.gr
Moutsos
Vassilios I
VI
Lampropoulou
Maria
M
Little
James L
JL
Hyatt
John A
JA
D002839:Chromans / Q000138:chemical synthesis / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism; D014810:Vitamin E / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D002839:Chromans; D014810:Vitamin E; C082097:tocotrienol, delta; C013649:plastochromanol 8; C082089:tocotrienol, beta; D000432:Methanol