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

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...

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Bibliographic Details
Main Authors: Jörg Erdsack, Norbert Krause
Format: Article
Language:English
Published: Beilstein-Institut 2013-09-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
allenes
amino acids
cuprates
furanomycin
gold catalysis
Online Access:https://doi.org/10.3762/bjoc.9.229
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spelling doaj-1a7cdc144aa2450eb3a36f4fdabe95362021-02-02T02:31:42ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-09-01911936194210.3762/bjoc.9.2291860-5397-9-229An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycineJörg Erdsack0Norbert Krause1Organic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, GermanyOrganic Chemistry, Dortmund University of Technology, Otto-Hahn-Strasse 6, D-44227 Dortmund, GermanyThe 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.https://doi.org/10.3762/bjoc.9.229allenesamino acidscupratesfuranomycingold catalysis
collection DOAJ
language English
format Article
sources DOAJ
author Jörg Erdsack
Norbert Krause
spellingShingle Jörg Erdsack
Norbert Krause
An approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αS,2R)-(2,5-dihydro-1H-pyrrol-2-yl)glycine
Beilstein Journal of Organic Chemistry
allenes
amino acids
cuprates
furanomycin
gold catalysis
author_facet Jörg Erdsack
Norbert Krause
author_sort Jörg Erdsack
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_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_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_sort approach towards azafuranomycin analogs by gold-catalyzed cycloisomerization of allenes: synthesis of (αs,2r)-(2,5-dihydro-1h-pyrrol-2-yl)glycine
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2013-09-01
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.
topic allenes
amino acids
cuprates
furanomycin
gold catalysis
url https://doi.org/10.3762/bjoc.9.229
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