Couladouros Elias A, Moutsos Vassilios I, Lampropoulou Maria, Little James L, Hyatt John A
Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, GR 118 55 Athens, Greece.
J Org Chem. 2007 Aug 31;72(18):6735-41. doi: 10.1021/jo0705418. Epub 2007 Aug 9.
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.
使用廉价的市售原料，已高收率地制备了天然β-、γ-和δ-生育三烯酚的色满甲醇前体。酶促拆分以高对映体过量得到手性色满甲醇。随后法尼基侧链的连接产率很高，从而能够在一个最终步骤中制备不对称的β-、γ-和δ-生育三烯酚，该步骤中同时发生酚的脱保护和砜基的去除。这种化学方法首次合成了天然系列的β-生育三烯酚。
