Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow

A short total synthesis of ajoene, (E,Z)‐4,5,9‐trithiadodeca‐1,6,11‐triene 9‐oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z)‐4,5,9‐trithiadodeca‐1,7,11‐triene is described starting from simple and easily accessible starting ma...

Descripción completa

Detalles Bibliográficos
Autores principales: Raynbird, Marina Yamamoto, Silva, Filipa, Smallman, Harry, Khokhar, Shaista S., Neef, Daniel, Evans, Gareth J. S., Wirth, Thomas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384054/
https://www.ncbi.nlm.nih.gov/pubmed/32364668
http://dx.doi.org/10.1002/chem.202001598
_version_ 1783563546386235392
author Raynbird, Marina Yamamoto
Silva, Filipa
Smallman, Harry
Khokhar, Shaista S.
Neef, Daniel
Evans, Gareth J. S.
Wirth, Thomas
author_facet Raynbird, Marina Yamamoto
Silva, Filipa
Smallman, Harry
Khokhar, Shaista S.
Neef, Daniel
Evans, Gareth J. S.
Wirth, Thomas
author_sort Raynbird, Marina Yamamoto
collection PubMed
description A short total synthesis of ajoene, (E,Z)‐4,5,9‐trithiadodeca‐1,6,11‐triene 9‐oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z)‐4,5,9‐trithiadodeca‐1,7,11‐triene is described starting from simple and easily accessible starting materials. Over four steps including propargylation, radical addition of thioacetate, deprotection, and disulfide formation/ allylation, the target product can be obtained at a rate of 0.26 g h(−1) in an overall yield of 12 %.
format Online
Article
Text
id pubmed-7384054
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-73840542020-07-28 Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow Raynbird, Marina Yamamoto Silva, Filipa Smallman, Harry Khokhar, Shaista S. Neef, Daniel Evans, Gareth J. S. Wirth, Thomas Chemistry Communications A short total synthesis of ajoene, (E,Z)‐4,5,9‐trithiadodeca‐1,6,11‐triene 9‐oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z)‐4,5,9‐trithiadodeca‐1,7,11‐triene is described starting from simple and easily accessible starting materials. Over four steps including propargylation, radical addition of thioacetate, deprotection, and disulfide formation/ allylation, the target product can be obtained at a rate of 0.26 g h(−1) in an overall yield of 12 %. John Wiley and Sons Inc. 2020-06-15 2020-07-08 /pmc/articles/PMC7384054/ /pubmed/32364668 http://dx.doi.org/10.1002/chem.202001598 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Raynbird, Marina Yamamoto
Silva, Filipa
Smallman, Harry
Khokhar, Shaista S.
Neef, Daniel
Evans, Gareth J. S.
Wirth, Thomas
Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow
title Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow
title_full Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow
title_fullStr Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow
title_full_unstemmed Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow
title_short Short Total Synthesis of Ajoene, (E,Z)‐4,5,9‐Trithiadodeca‐1,6,11‐triene 9‐oxide, in Batch and (E,Z)‐4,5,9‐Trithiadodeca‐1,7,11‐triene in Continuous Flow
title_sort short total synthesis of ajoene, (e,z)‐4,5,9‐trithiadodeca‐1,6,11‐triene 9‐oxide, in batch and (e,z)‐4,5,9‐trithiadodeca‐1,7,11‐triene in continuous flow
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7384054/
https://www.ncbi.nlm.nih.gov/pubmed/32364668
http://dx.doi.org/10.1002/chem.202001598
work_keys_str_mv AT raynbirdmarinayamamoto shorttotalsynthesisofajoeneez459trithiadodeca1611triene9oxideinbatchandez459trithiadodeca1711trieneincontinuousflow
AT silvafilipa shorttotalsynthesisofajoeneez459trithiadodeca1611triene9oxideinbatchandez459trithiadodeca1711trieneincontinuousflow
AT smallmanharry shorttotalsynthesisofajoeneez459trithiadodeca1611triene9oxideinbatchandez459trithiadodeca1711trieneincontinuousflow
AT khokharshaistas shorttotalsynthesisofajoeneez459trithiadodeca1611triene9oxideinbatchandez459trithiadodeca1711trieneincontinuousflow
AT neefdaniel shorttotalsynthesisofajoeneez459trithiadodeca1611triene9oxideinbatchandez459trithiadodeca1711trieneincontinuousflow
AT evansgarethjs shorttotalsynthesisofajoeneez459trithiadodeca1611triene9oxideinbatchandez459trithiadodeca1711trieneincontinuousflow
AT wirththomas shorttotalsynthesisofajoeneez459trithiadodeca1611triene9oxideinbatchandez459trithiadodeca1711trieneincontinuousflow

Ejemplares similares