Cargando…

Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy

Heating aldehydes that contain a protected hydroxymethyl group, a tethered alkyl chloride and a tethered alkenyl group at the α-position of the aldehyde with an amine sets up a cascade (tandem) reaction sequence involving condensation to an intermediate imine, then cyclization and formation of an in...

Descripción completa

Detalles Bibliográficos
Autores principales: Coldham, Iain, Burrell, Adam J M, Guerrand, Hélène D S, Watson, Luke, Martin, Nathaniel G, Oram, Niall
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302069/
https://www.ncbi.nlm.nih.gov/pubmed/22423277
http://dx.doi.org/10.3762/bjoc.8.11
_version_ 1782226628898717696
author Coldham, Iain
Burrell, Adam J M
Guerrand, Hélène D S
Watson, Luke
Martin, Nathaniel G
Oram, Niall
author_facet Coldham, Iain
Burrell, Adam J M
Guerrand, Hélène D S
Watson, Luke
Martin, Nathaniel G
Oram, Niall
author_sort Coldham, Iain
collection PubMed
description Heating aldehydes that contain a protected hydroxymethyl group, a tethered alkyl chloride and a tethered alkenyl group at the α-position of the aldehyde with an amine sets up a cascade (tandem) reaction sequence involving condensation to an intermediate imine, then cyclization and formation of an intermediate azomethine ylide and then intramolecular dipolar cycloaddition. The fused tricyclic products are formed with complete or very high stereochemical control. The hydroxymethyl group was converted into an aldehyde – which could be removed to give the tricyclic amine products that are unsubstituted at the ring junction positions – or was converted into an alkene, which allowed the formation of the core ring system of the alkaloids scandine and meloscine.
format Online
Article
Text
id pubmed-3302069
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-33020692012-03-15 Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy Coldham, Iain Burrell, Adam J M Guerrand, Hélène D S Watson, Luke Martin, Nathaniel G Oram, Niall Beilstein J Org Chem Full Research Paper Heating aldehydes that contain a protected hydroxymethyl group, a tethered alkyl chloride and a tethered alkenyl group at the α-position of the aldehyde with an amine sets up a cascade (tandem) reaction sequence involving condensation to an intermediate imine, then cyclization and formation of an intermediate azomethine ylide and then intramolecular dipolar cycloaddition. The fused tricyclic products are formed with complete or very high stereochemical control. The hydroxymethyl group was converted into an aldehyde – which could be removed to give the tricyclic amine products that are unsubstituted at the ring junction positions – or was converted into an alkene, which allowed the formation of the core ring system of the alkaloids scandine and meloscine. Beilstein-Institut 2012-01-18 /pmc/articles/PMC3302069/ /pubmed/22423277 http://dx.doi.org/10.3762/bjoc.8.11 Text en Copyright © 2012, Coldham et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Coldham, Iain
Burrell, Adam J M
Guerrand, Hélène D S
Watson, Luke
Martin, Nathaniel G
Oram, Niall
Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
title Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
title_full Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
title_fullStr Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
title_full_unstemmed Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
title_short Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
title_sort synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302069/
https://www.ncbi.nlm.nih.gov/pubmed/22423277
http://dx.doi.org/10.3762/bjoc.8.11
work_keys_str_mv AT coldhamiain synthesisoffusedtricyclicaminesunsubstitutedattheringjunctionpositionsbyacascadecondensationcyclizationcycloadditionthendecarbonylationstrategy
AT burrelladamjm synthesisoffusedtricyclicaminesunsubstitutedattheringjunctionpositionsbyacascadecondensationcyclizationcycloadditionthendecarbonylationstrategy
AT guerrandheleneds synthesisoffusedtricyclicaminesunsubstitutedattheringjunctionpositionsbyacascadecondensationcyclizationcycloadditionthendecarbonylationstrategy
AT watsonluke synthesisoffusedtricyclicaminesunsubstitutedattheringjunctionpositionsbyacascadecondensationcyclizationcycloadditionthendecarbonylationstrategy
AT martinnathanielg synthesisoffusedtricyclicaminesunsubstitutedattheringjunctionpositionsbyacascadecondensationcyclizationcycloadditionthendecarbonylationstrategy
AT oramniall synthesisoffusedtricyclicaminesunsubstitutedattheringjunctionpositionsbyacascadecondensationcyclizationcycloadditionthendecarbonylationstrategy