Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization

[Image: see text] The total synthesis of lundurines A–C has been accomplished in racemic and enantiopure forms in 11–13 and 12–14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroar...

Descripción completa

Detalles Bibliográficos
Autores principales: Kirillova, Mariia S., Muratore, Michael E., Dorel, Ruth, Echavarren, Antonio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4819460/
https://www.ncbi.nlm.nih.gov/pubmed/26963149
http://dx.doi.org/10.1021/jacs.6b01428
_version_ 1782425200989569024
author Kirillova, Mariia S.
Muratore, Michael E.
Dorel, Ruth
Echavarren, Antonio M.
author_facet Kirillova, Mariia S.
Muratore, Michael E.
Dorel, Ruth
Echavarren, Antonio M.
author_sort Kirillova, Mariia S.
collection PubMed
description [Image: see text] The total synthesis of lundurines A–C has been accomplished in racemic and enantiopure forms in 11–13 and 12–14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.
format Online
Article
Text
id pubmed-4819460
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-48194602016-04-06 Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization Kirillova, Mariia S. Muratore, Michael E. Dorel, Ruth Echavarren, Antonio M. J Am Chem Soc [Image: see text] The total synthesis of lundurines A–C has been accomplished in racemic and enantiopure forms in 11–13 and 12–14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame. American Chemical Society 2016-03-10 2016-03-23 /pmc/articles/PMC4819460/ /pubmed/26963149 http://dx.doi.org/10.1021/jacs.6b01428 Text en Copyright © 2016 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kirillova, Mariia S.
Muratore, Michael E.
Dorel, Ruth
Echavarren, Antonio M.
Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
title Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
title_full Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
title_fullStr Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
title_full_unstemmed Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
title_short Concise Total Synthesis of Lundurines A–C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
title_sort concise total synthesis of lundurines a–c enabled by gold catalysis and a homodienyl retro-ene/ene isomerization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4819460/
https://www.ncbi.nlm.nih.gov/pubmed/26963149
http://dx.doi.org/10.1021/jacs.6b01428
work_keys_str_mv AT kirillovamariias concisetotalsynthesisoflundurinesacenabledbygoldcatalysisandahomodienylretroeneeneisomerization
AT muratoremichaele concisetotalsynthesisoflundurinesacenabledbygoldcatalysisandahomodienylretroeneeneisomerization
AT dorelruth concisetotalsynthesisoflundurinesacenabledbygoldcatalysisandahomodienylretroeneeneisomerization
AT echavarrenantoniom concisetotalsynthesisoflundurinesacenabledbygoldcatalysisandahomodienylretroeneeneisomerization

Ejemplares similares