Enantioselective synthesis of the Cyclopiazonic acid family using sulfur ylides
File(s)
Author(s)
Zhurakovskyi, Oleksandr
Tuerkmen, Yunus E
Loeffler, Lorenz E
Moorthie, Vijayalakshmi A
Chen, C Chun
Type
Journal Article
Abstract
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.
Date Issued
2018-01-09
Date Acceptance
2017-12-19
Citation
Angewandte Chemie International Edition, 2018, 57 (5), pp.1346-1350
ISSN
1521-3757
Publisher
Wiley
Start Page
1346
End Page
1350
Journal / Book Title
Angewandte Chemie International Edition
Volume
57
Issue
5
Copyright Statement
© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited (https://creativecommons.org/licenses/by/4.0/).
License URL
Identifier
http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000422940600037&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=1ba7043ffcc86c417c072aa74d649202
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
(3+2)-cycloaddition
aziridination
sulfur ylide
total synthesis
alpha-cyclopiazonic acid
FORMAL 3+2 CYCLOADDITION
PENICILLIUM-CYCLOPIUM
(+/-)-ALPHA-CYCLOPIAZONIC ACID
ASPERGILLUS-FLAVUS
PROTON REMOVAL
STERIC COURSE
BIOSYNTHESIS
DERIVATIVES
CYCLIZATION
AZIRIDINES
Publication Status
Published
Date Publish Online
2017-12-19