Rao Pemmaraju N, Cessac James W
Department of Organic Chemistry, Southwest Foundation for Biomedical Research, P O Box 760549, 7620 N W Loop 410 (at Military Drive), San Antonio, TX 78227-5301, USA.
Steroids. 2002 Dec;67(13-14):1065-70. doi: 10.1016/s0039-128x(02)00065-x.
An efficient and practical approach to synthesize moderate to large amounts of 2-methoxyestradiol (2-ME2) is described. The key step in the synthesis is the regioselective introduction of an acetyl group at the C-2 position of estradiol using a zirconium tetrachloride mediated Fries rearrangement carried out on estradiol diacetate. The seven step synthetic procedure readily gave 2-ME2 in 49% overall yield. Application of this method to the synthesis of 2-methoxy-7 alpha-methylestradiol is also described.
描述了一种高效实用的方法来合成中等至大量的2-甲氧基雌二醇（2-ME2）。合成中的关键步骤是在雌二醇二乙酸酯上进行四氯化锆介导的弗里斯重排，在雌二醇的C-2位区域选择性引入乙酰基。该七步合成程序以49%的总收率轻松得到2-ME2。还描述了该方法在合成2-甲氧基-7α-甲基雌二醇中的应用。
