Total Syntheses of Periconiasins A-E.
The first and collective total syntheses of periconiasins A-E, a group of naturally occurring cytochalasans, were achieved by a series of rationally designed or bioinspired transformations. Salient features of the syntheses include a tandem aldol condensation/Grob fragmentation to assemble the linear polyketide-amino acid hybrid precursor, a Diels-Alder macrocylization to construct the 9/6/5 tricyclic core of periconiasins A-C, and a transannular carbonyl-ene reaction to forge the polycyclic framework of periconiasins D and E.
School of Pharmaceutical Sciences & Comprehensive AIDS Research Center, Tsinghua University, Beijing, 100084, China.|Tsinghua-Peking Center for Life Sciences, School of Life Sciences, Tsinghua University, Beijing, 100084, P.R. China.
Chong
C
Tian
School of Pharmaceutical Sciences & Comprehensive AIDS Research Center, Tsinghua University, Beijing, 100084, China.
Xiaoqiang
X
Lei
School of Pharmaceutical Sciences & Comprehensive AIDS Research Center, Tsinghua University, Beijing, 100084, China.
Yuanhao
Y
Wang
School of Pharmaceutical Sciences & Comprehensive AIDS Research Center, Tsinghua University, Beijing, 100084, China.
Zhen
Z
Dong
School of Pharmaceutical Sciences & Comprehensive AIDS Research Center, Tsinghua University, Beijing, 100084, China. gangliu27@tsinghua.edu.cn.|Tsinghua-Peking Center for Life Sciences, School of Life Sciences, Tsinghua University, Beijing, 100084, P.R. China. gangliu27@tsinghua.edu.cn.
Gang
G
Liu
School of Pharmaceutical Sciences & Comprehensive AIDS Research Center, Tsinghua University, Beijing, 100084, China. yefengtang@tsinghua.edu.cn.|Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu, 610041, China. yefengtang@tsinghua.edu.cn.
Yefeng
0000-0002-6223-0608
Y
Tang
biomimetic synthesis; cycloaddition; natural products; polyketides; total synthesis