Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones

Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselect...

Descripción completa

Detalles Bibliográficos
Autores principales: Throup, Adam, Patterson, Laurence H., Sheldrake, Helen M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5066561/
https://www.ncbi.nlm.nih.gov/pubmed/27722445
http://dx.doi.org/10.1039/c6ob01661h
_version_ 1782460507855257600
author Throup, Adam
Patterson, Laurence H.
Sheldrake, Helen M.
author_facet Throup, Adam
Patterson, Laurence H.
Sheldrake, Helen M.
author_sort Throup, Adam
collection PubMed
description Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity.
format Online
Article
Text
id pubmed-5066561
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-50665612016-10-19 Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones Throup, Adam Patterson, Laurence H. Sheldrake, Helen M. Org Biomol Chem Chemistry Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity. Royal Society of Chemistry 2016-10-28 2016-09-20 /pmc/articles/PMC5066561/ /pubmed/27722445 http://dx.doi.org/10.1039/c6ob01661h Text en This journal is © The Royal Society of Chemistry 2016 https://creativecommons.org/licenses/by/3.0/This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/ (https://creativecommons.org/licenses/by/3.0/) ) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Throup, Adam
Patterson, Laurence H.
Sheldrake, Helen M.
Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones
title Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones
title_full Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones
title_fullStr Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones
title_full_unstemmed Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones
title_short Intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones
title_sort intramolecular thermal stepwise [2 + 2] cycloadditions: investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5066561/
https://www.ncbi.nlm.nih.gov/pubmed/27722445
http://dx.doi.org/10.1039/c6ob01661h
work_keys_str_mv AT throupadam intramolecularthermalstepwise22cycloadditionsinvestigationofastereoselectivesynthesisofn20bicyclolactones
AT pattersonlaurenceh intramolecularthermalstepwise22cycloadditionsinvestigationofastereoselectivesynthesisofn20bicyclolactones
AT sheldrakehelenm intramolecularthermalstepwise22cycloadditionsinvestigationofastereoselectivesynthesisofn20bicyclolactones

Ejemplares similares