Takao Ken-Ichi, Nemoto Ryuichi, Mori Kento, Namba Ayumi, Yoshida Keisuke, Ogura Akihiro
Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
Chemistry. 2017 Mar 17;23(16):3828-3831. doi: 10.1002/chem.201700483. Epub 2017 Feb 23.
A structural revision of clavilactone D, a potent inhibitor of protein tyrosine kinases, was achieved by total syntheses of two newly proposed structures. The syntheses relied on ring-opening/ring-closing metathesis, which transformed a cyclobutenecarboxylate into a γ-butenolide. The syntheses confirmed that the correct structure of clavilactone D has an amino group at C-3 instead of a hydroxy group at C-2 in the originally proposed structure.
通过对两种新提出结构的全合成，实现了对蛋白酪氨酸激酶强效抑制剂克拉维内酯D的结构修正。合成过程依赖于开环/闭环复分解反应，该反应将环丁烯羧酸盐转化为γ-丁内酯。合成结果证实，克拉维内酯D的正确结构在C-3位有一个氨基，而不是最初提出结构中C-2位的羟基。
