Takao K I, Sasaki T, Kozaki T, Yanagisawa Y, Tadano K I, Kawashima A, Shinonaga H
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Org Lett. 2001 Dec 27;3(26):4291-4. doi: 10.1021/ol016960n.
The first syntheses of new antibiotics UPA0043 and UPA0044 were accomplished starting from commercially available 18beta-glycyrrhetinic acid and vanillin. The present syntheses involve the coupling of a sesquiterpenoid aldehyde and an aryllithium, the stereoselective formation of a p-quinone-methide system, and regioselective intramolecular cyclization via an epoxy ring opening. [reaction: see text]
新型抗生素UPA0043和UPA0044的首次合成是从市售的18β-甘草次酸和香草醛开始完成的。目前的合成涉及倍半萜醛与芳基锂的偶联、对苯醌甲基化物体系的立体选择性形成以及通过环氧开环的区域选择性分子内环化。[反应：见正文]
