An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine

The synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of α-aminoallene 17 is described. The target molecule was synthesized in 13 linear steps from Cbz-protected Garner aldehyde (R)-2 in an overall yield of 2.4%. The appro...

Descripción completa

Detalles Bibliográficos
Autores principales: Erdsack, Jörg, Krause, Norbert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817573/
https://www.ncbi.nlm.nih.gov/pubmed/24204404
http://dx.doi.org/10.3762/bjoc.9.229
_version_ 1782478092107776000
author Erdsack, Jörg
Krause, Norbert
author_facet Erdsack, Jörg
Krause, Norbert
author_sort Erdsack, Jörg
collection PubMed
description The synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of α-aminoallene 17 is described. The target molecule was synthesized in 13 linear steps from Cbz-protected Garner aldehyde (R)-2 in an overall yield of 2.4%. The approach was first examined in model studies, which afforded the alkylated azafuranomycin derivative 13a in 2.9% yield over 12 steps.
format Online
Article
Text
id pubmed-3817573
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-38175732013-11-07 An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine Erdsack, Jörg Krause, Norbert Beilstein J Org Chem Full Research Paper The synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine (22, normethylazafuranomycin) by the gold-catalyzed cycloisomerization of α-aminoallene 17 is described. The target molecule was synthesized in 13 linear steps from Cbz-protected Garner aldehyde (R)-2 in an overall yield of 2.4%. The approach was first examined in model studies, which afforded the alkylated azafuranomycin derivative 13a in 2.9% yield over 12 steps. Beilstein-Institut 2013-09-25 /pmc/articles/PMC3817573/ /pubmed/24204404 http://dx.doi.org/10.3762/bjoc.9.229 Text en Copyright © 2013, Erdsack and Krause 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
Erdsack, Jörg
Krause, Norbert
An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
title An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
title_full An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
title_fullStr An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
title_full_unstemmed An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
title_short An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
title_sort approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αs,2r)-(2,5-dihydro-1h-pyrrol-2-yl)glycine
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3817573/
https://www.ncbi.nlm.nih.gov/pubmed/24204404
http://dx.doi.org/10.3762/bjoc.9.229
work_keys_str_mv AT erdsackjorg anapproachtowardsazafuranomycinanalogsbygoldcatalyzedcycloisomerizationofallenessynthesisofas2r25dihydro1hpyrrol2ylglycine
AT krausenorbert anapproachtowardsazafuranomycinanalogsbygoldcatalyzedcycloisomerizationofallenessynthesisofas2r25dihydro1hpyrrol2ylglycine
AT erdsackjorg approachtowardsazafuranomycinanalogsbygoldcatalyzedcycloisomerizationofallenessynthesisofas2r25dihydro1hpyrrol2ylglycine
AT krausenorbert approachtowardsazafuranomycinanalogsbygoldcatalyzedcycloisomerizationofallenessynthesisofas2r25dihydro1hpyrrol2ylglycine

Ejemplares similares