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
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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.
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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

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