Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials

[Image: see text] Here we present a polycyclization of oxotriphenylhexanoates. The polycyclization is governed by electronic effects, and three major synthetic paths have been established leading to stereochemically complex tricyclic frameworks with up to five stereogenic centers. The method is comp...

Descripción completa

Detalles Bibliográficos
Autores principales: Kamlar, Martin, Runemark, August, Císařová, Ivana, Sundén, Henrik
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7660947/
https://www.ncbi.nlm.nih.gov/pubmed/33079554
http://dx.doi.org/10.1021/acs.orglett.0c03020
_version_ 1783609118870732800
author Kamlar, Martin
Runemark, August
Císařová, Ivana
Sundén, Henrik
author_facet Kamlar, Martin
Runemark, August
Císařová, Ivana
Sundén, Henrik
author_sort Kamlar, Martin
collection PubMed
description [Image: see text] Here we present a polycyclization of oxotriphenylhexanoates. The polycyclization is governed by electronic effects, and three major synthetic paths have been established leading to stereochemically complex tricyclic frameworks with up to five stereogenic centers. The method is compatible with an array of functional groups, allowing pharmacophoric elements to be introduced post cyclization.
format Online
Article
Text
id pubmed-7660947
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-76609472020-11-13 Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials Kamlar, Martin Runemark, August Císařová, Ivana Sundén, Henrik Org Lett [Image: see text] Here we present a polycyclization of oxotriphenylhexanoates. The polycyclization is governed by electronic effects, and three major synthetic paths have been established leading to stereochemically complex tricyclic frameworks with up to five stereogenic centers. The method is compatible with an array of functional groups, allowing pharmacophoric elements to be introduced post cyclization. American Chemical Society 2020-10-20 2020-11-06 /pmc/articles/PMC7660947/ /pubmed/33079554 http://dx.doi.org/10.1021/acs.orglett.0c03020 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Kamlar, Martin
Runemark, August
Císařová, Ivana
Sundén, Henrik
Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
title Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
title_full Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
title_fullStr Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
title_full_unstemmed Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
title_short Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials
title_sort polycyclizations of ketoesters: synthesis of complex tricycles with up to five stereogenic centers from available starting materials
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7660947/
https://www.ncbi.nlm.nih.gov/pubmed/33079554
http://dx.doi.org/10.1021/acs.orglett.0c03020
work_keys_str_mv AT kamlarmartin polycyclizationsofketoesterssynthesisofcomplextricycleswithuptofivestereogeniccentersfromavailablestartingmaterials
AT runemarkaugust polycyclizationsofketoesterssynthesisofcomplextricycleswithuptofivestereogeniccentersfromavailablestartingmaterials
AT cisarovaivana polycyclizationsofketoesterssynthesisofcomplextricycleswithuptofivestereogeniccentersfromavailablestartingmaterials
AT sundenhenrik polycyclizationsofketoesterssynthesisofcomplextricycleswithuptofivestereogeniccentersfromavailablestartingmaterials

Ejemplares similares