Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A

[Image: see text] Natural products containing aminocyclopentanes are common secondary metabolites, often biologically active. This work aims at the preparation of a useful synthon for total synthesis containing orthogonally protected amines. To this end, furfural and two amines were employed to form...

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Autores principales: Gomes, Rafael F. A., Vale, João R., Pereira, Juliana G., Afonso, Carlos A. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262273/
https://www.ncbi.nlm.nih.gov/pubmed/37249264
http://dx.doi.org/10.1021/acs.orglett.3c01513
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author Gomes, Rafael F. A.
Vale, João R.
Pereira, Juliana G.
Afonso, Carlos A. M.
author_facet Gomes, Rafael F. A.
Vale, João R.
Pereira, Juliana G.
Afonso, Carlos A. M.
author_sort Gomes, Rafael F. A.
collection PubMed
description [Image: see text] Natural products containing aminocyclopentanes are common secondary metabolites, often biologically active. This work aims at the preparation of a useful synthon for total synthesis containing orthogonally protected amines. To this end, furfural and two amines were employed to form mixed trans-4,5-diaminocyclopentenones promoted by Cu(OTf)(2). The selected amines can be orthogonally deprotected, allowing selective modification of the amines on the cyclopentane core. Their utility was showcased for the total synthesis of highly complex (±)-Agelastatin A.
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spelling pubmed-102622732023-06-15 Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A Gomes, Rafael F. A. Vale, João R. Pereira, Juliana G. Afonso, Carlos A. M. Org Lett [Image: see text] Natural products containing aminocyclopentanes are common secondary metabolites, often biologically active. This work aims at the preparation of a useful synthon for total synthesis containing orthogonally protected amines. To this end, furfural and two amines were employed to form mixed trans-4,5-diaminocyclopentenones promoted by Cu(OTf)(2). The selected amines can be orthogonally deprotected, allowing selective modification of the amines on the cyclopentane core. Their utility was showcased for the total synthesis of highly complex (±)-Agelastatin A. American Chemical Society 2023-05-30 /pmc/articles/PMC10262273/ /pubmed/37249264 http://dx.doi.org/10.1021/acs.orglett.3c01513 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Gomes, Rafael F. A.
Vale, João R.
Pereira, Juliana G.
Afonso, Carlos A. M.
Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A
title Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A
title_full Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A
title_fullStr Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A
title_full_unstemmed Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A
title_short Orthogonally Protected Diaminocyclopentenones as Synthons: Total Synthesis of (±)-Agelastatin A
title_sort orthogonally protected diaminocyclopentenones as synthons: total synthesis of (±)-agelastatin a
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10262273/
https://www.ncbi.nlm.nih.gov/pubmed/37249264
http://dx.doi.org/10.1021/acs.orglett.3c01513
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