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^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

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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	9 Jan 2018
DOIs	https://doi.org/10.1002/anie.201712065
Publication status	Published - 22 Jan 2018

Keywords

(3+2)-cycloaddition
Aziridination
Sulfur ylide
Total synthesis
α-cyclopiazonic acid

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FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds
Aggarwal, V. K. (Principal Investigator)
1/10/15 → 31/03/21
Project: Research
A 13C NMR Coldprobe to Underpin Chemistry Research.
Butts, C. P. (Principal Investigator)
28/02/14 → 29/11/17
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research

Professor Varinder K Aggarwal
- V.Aggarwalbristol.acuk
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
Person: Academic

Cite this

Zhurakovskyi, O., Türkmen, Y. E., Löffler, L. E., Moorthie, V. A., Chen, C. C., Shaw, M. A., Crimmin, M. R., Ferrara, M., Ahmad, M., Ostovar, M., Matlock, J. V., & Aggarwal, V. K. (2018). Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides. Angewandte Chemie - International Edition, 57(5), 1346–1350. https://doi.org/10.1002/anie.201712065

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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.",

keywords = "(3+2)-cycloaddition, Aziridination, Sulfur ylide, Total synthesis, α-cyclopiazonic acid",

author = "Oleksandr Zhurakovskyi and T{\"u}rkmen, {Yunus E.} and L{\"o}ffler, {Lorenz E.} and Moorthie, {Vijayalakshmi A.} and Chen, {C. Chun} and Shaw, {Michael A.} and Crimmin, {Mark R.} and Marco Ferrara and Mushtaq Ahmad and Mehrnoosh Ostovar and Matlock, {Johnathan V.} and Aggarwal, {Varinder K.}",

year = "2018",

month = jan,

day = "22",

doi = "10.1002/anie.201712065",

language = "English",

volume = "57",

pages = "1346–1350",

journal = "Angewandte Chemie - International Edition",

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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.

PY - 2018/1/22

Y1 - 2018/1/22

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.

KW - (3+2)-cycloaddition

KW - Aziridination

KW - Sulfur ylide

KW - Total synthesis

KW - α-cyclopiazonic acid

U2 - 10.1002/anie.201712065

DO - 10.1002/anie.201712065

M3 - Article (Academic Journal)

C2 - 29265694

AN - SCOPUS:85040160842

SN - 1433-7851

VL - 57

SP - 1346

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

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Projects

FRESCO: Efficient, Flexible Synthesis of Molecules with Tailored Shapes: from Photoswitchable Helices to anti-Cancer Compounds

A 13C NMR Coldprobe to Underpin Chemistry Research.

3-month Core Capability for Chemistry Research

Profiles

Professor Varinder K Aggarwal

Cite this