Synthesis of the B-seco limonoid core scaffold

Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C...

Descripción completa

Detalles Bibliográficos
Autores principales: Bruss, Hanna, Schuster, Hannah, Martinez, Rémi, Kaiser, Markus, Antonchick, Andrey P, Waldmann, Herbert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943702/
https://www.ncbi.nlm.nih.gov/pubmed/24605139
http://dx.doi.org/10.3762/bjoc.10.15
_version_ 1782306294187687936
author Bruss, Hanna
Schuster, Hannah
Martinez, Rémi
Kaiser, Markus
Antonchick, Andrey P
Waldmann, Herbert
author_facet Bruss, Hanna
Schuster, Hannah
Martinez, Rémi
Kaiser, Markus
Antonchick, Andrey P
Waldmann, Herbert
author_sort Bruss, Hanna
collection PubMed
description Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems.
format Online
Article
Text
id pubmed-3943702
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-39437022014-03-06 Synthesis of the B-seco limonoid core scaffold Bruss, Hanna Schuster, Hannah Martinez, Rémi Kaiser, Markus Antonchick, Andrey P Waldmann, Herbert Beilstein J Org Chem Full Research Paper Synthetic investigations towards the structurally complex and highly decorated framework of B-seco limonoid natural products by means of a [3,3]-sigmatropic rearrangement are described. Detailed model studies reveal, that an Ireland–Claisen rearrangement can be employed to construct the central C9–C10 bond thereby giving access to the B-seco limonoid scaffold. However, application of the developed strategy ended up failing in more complex and sterically demanding systems. Beilstein-Institut 2014-01-16 /pmc/articles/PMC3943702/ /pubmed/24605139 http://dx.doi.org/10.3762/bjoc.10.15 Text en Copyright © 2014, Bruss 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
Bruss, Hanna
Schuster, Hannah
Martinez, Rémi
Kaiser, Markus
Antonchick, Andrey P
Waldmann, Herbert
Synthesis of the B-seco limonoid core scaffold
title Synthesis of the B-seco limonoid core scaffold
title_full Synthesis of the B-seco limonoid core scaffold
title_fullStr Synthesis of the B-seco limonoid core scaffold
title_full_unstemmed Synthesis of the B-seco limonoid core scaffold
title_short Synthesis of the B-seco limonoid core scaffold
title_sort synthesis of the b-seco limonoid core scaffold
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943702/
https://www.ncbi.nlm.nih.gov/pubmed/24605139
http://dx.doi.org/10.3762/bjoc.10.15
work_keys_str_mv AT brusshanna synthesisofthebsecolimonoidcorescaffold
AT schusterhannah synthesisofthebsecolimonoidcorescaffold
AT martinezremi synthesisofthebsecolimonoidcorescaffold
AT kaisermarkus synthesisofthebsecolimonoidcorescaffold
AT antonchickandreyp synthesisofthebsecolimonoidcorescaffold
AT waldmannherbert synthesisofthebsecolimonoidcorescaffold

Ejemplares similares