Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Oleksandr Zhurakovskyi; Yunus E Türkmen; Lorenz E Löffler; Vijayalakshmi A Moorthie; C Chun Chen; Michael A Shaw; Mark R Crimmin; Marco Ferrara; Mushtaq Ahmad; Mehrnoosh Ostovar; Johnathan V Matlock; Varinder K Aggarwal

doi:10.1002/anie.201712065

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Oleksandr Zhurakovskyi
, Yunus E Türkmen
, Lorenz E Löffler
, Vijayalakshmi A Moorthie
, C Chun Chen
, Michael A Shaw
, Mark R Crimmin
, Marco Ferrara
, Mushtaq Ahmad
, Mehrnoosh Ostovar
, Johnathan V Matlock
, Varinder K Aggarwal

Centre for Research in Mechanisms of Disease and Drug Discovery

Research output: Contribution to journal › Article › peer-review

41 Citations (Scopus)

24 Downloads (Pure)

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.

Original language	English
Pages (from-to)	1346-1350
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	57
Issue number	5
Early online date	19 Dec 2017
DOIs	https://doi.org/10.1002/anie.201712065
Publication status	Published - 26 Jan 2018

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© 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/
Final published version, 3.07 MBLicence: CC BY

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title = "Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides",

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.",

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note = "{\textcopyright} 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/",

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doi = "10.1002/anie.201712065",

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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

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EP - 1350

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 5

ER -

Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Abstract

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