Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9, 1060 Vienna, Austria.
Institute for Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9, 1060 Vienna, Austria.
Org Biomol Chem. 2018 Apr 4;16(14):2508-2521. doi: 10.1039/C8OB00122G.
The human urinary long-term metabolite "M3" (4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrost-13-en-3-ol) of the common doping agent DHCMT has thus far been detected via GC/MS-MS, creating ambiguities concerning its absolute configuration. Its structure was elucidated via the synthesis of all eight possible stereoisomers with 17β-hydroxymethyl configuration. The highlights of the synthesis consist of a novel first generation approach to 4β-chloro-5β compounds as well as a divergent route which allows easy access to the remaining A-ring chlorohydrins.
人类尿液中常见兴奋剂 DHCMT 的长期代谢产物“M3”（4-氯-17β-羟甲基-17α-甲基-18-去甲雄甾-13-烯-3-醇）已通过 GC/MS-MS 检测到，这使其绝对构型存在歧义。通过合成具有 17β-羟甲基构型的全部八个可能的立体异构体，阐明了其结构。该合成的重点包括一种新颖的第一代方法来合成 4β-氯-5β 化合物，以及一种发散途径，可轻松获得其余 A 环氯醇。
