Bracher F, Litz T
Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig, Germany.
Bioorg Med Chem. 1996 Jun;4(6):877-80. doi: 10.1016/0968-0896(96)00077-6.
(S)-1-Phenyl-3-buten-1-ol (1), prepared in high optical purity by enzymatic resolution of the racemate, is a convenient building block for the synthesis of (R)-fluoxetine (7a) and (R)-tomoxetine (7b). Compound 1 was converted to the title drugs by etherification with appropriate phenols under Mitsunobu conditions, ozonolysis of the terminal double bond, mesylation of the resulting alcohol and substitution with methylamine.
通过外消旋体的酶促拆分以高光学纯度制备的(S)-1-苯基-3-丁烯-1-醇(1)，是合成(R)-氟西汀(7a)和(R)-托莫西汀(7b)的便利结构单元。化合物1在光延反应条件下与适当的酚进行醚化反应，将末端双键进行臭氧分解，所得醇进行甲磺酰化，然后用甲胺进行取代反应，从而转化为标题药物。
