Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides
Zhurakovskyi, Oleksandr, Türkmen, Yunus E, Löffler, Lorenz E, Moorthie, Vijayalakshmi A, Chen, C Chun, Shaw, Michael A, Crimmin, Mark R, Ferrara, Marco, Ahmad, Mushtaq, Ostovar, Mehrnoosh, Matlock, Johnathan V and Aggarwal, Varinder K
(2018)
Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides.
Angewandte Chemie International Edition, 57 (5).
pp. 1346-1350.
ISSN 1433-7851
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.
Item Type | Article |
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Additional information | © 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/ |
Date Deposited | 15 May 2025 15:13 |
Last Modified | 31 May 2025 00:39 |