TY - JOUR
T1 - Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
AU - Zhurakovskyi, Oleksandr
AU - Türkmen, Yunus E
AU - Löffler, Lorenz E
AU - Moorthie, Vijayalakshmi A
AU - Chen, C Chun
AU - Shaw, Michael A
AU - Crimmin, Mark R
AU - Ferrara, Marco
AU - Ahmad, Mushtaq
AU - Ostovar, Mehrnoosh
AU - Matlock, Johnathan V
AU - Aggarwal, Varinder K
N1 - © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article distributed under the terms of the Creative Commons Attribution License (CC BY), https://creativecommons.org/licenses/by/4.0/
PY - 2018/1/26
Y1 - 2018/1/26
N2 - A convergent, nine-step (LLS), enantioselective synthesis of α-cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N-O cleavage of a bromoisoxazole.
AB - A convergent, nine-step (LLS), enantioselective synthesis of α-cyclopiazonic acid and related natural products is reported. The route features a) an enantioselective aziridination of an imine with a chiral sulfur ylide; b) a bioinspired (3+2)-cycloaddition of the aziridine onto an alkene; and c) installation of the acetyltetramic acid by an unprecedented tandem carbonylative lactamization/N-O cleavage of a bromoisoxazole.
U2 - 10.1002/anie.201712065
DO - 10.1002/anie.201712065
M3 - Article
C2 - 29265694
SN - 1433-7851
VL - 57
SP - 1346
EP - 1350
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
IS - 5
ER -