Gao Zhenhua, Li Junchen, Song Yunyang, Bi Xiaojing, Meng Xiangyan, Guo Yongbiao
State Key Laboratory of NBC Protection for Civilian Research Beijing 102205 P. R. China
RSC Adv. 2020 Oct 26;10(64):39266-39270. doi: 10.1039/d0ra08726b. eCollection 2020 Oct 21.
(+)-Crambescin A belongs to the polycyclic guanidine natural product family and has been shown to possess various medically important properties. The chiral bicyclic guanidine structure of (+)-crambescin A presents a challenge for chemical synthesis. Here we implement a novel asymmetric Biginelli reaction strategy to achieve the enantiospecific total synthesis of (+)-crambescin A in only 8 steps from the abundant and inexpensive aliphatic aldehyde, urea and methyl 3-oxobutanoate.
(+)-Crambescin A属于多环胍类天然产物家族，已被证明具有多种重要的医学特性。(+)-Crambescin A的手性双环胍结构对化学合成提出了挑战。在此，我们实施了一种新颖的不对称Biginelli反应策略，仅从丰富且廉价的脂肪醛、尿素和3-氧代丁酸甲酯出发，经过8步反应实现了(+)-Crambescin A的对映体特异性全合成。
