Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision

The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling (for Trp‐2‐CO(2)H) and Blaise reaction (for Pyrr). An incorrect assignment of the pyrrolid...

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Autores principales: Melikhova, Ekaterina Y., Pullin, Robert D. C., Winter, Christian, Donohoe, Timothy J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5132153/
https://www.ncbi.nlm.nih.gov/pubmed/27418203
http://dx.doi.org/10.1002/anie.201604764
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author Melikhova, Ekaterina Y.
Pullin, Robert D. C.
Winter, Christian
Donohoe, Timothy J.
author_facet Melikhova, Ekaterina Y.
Pullin, Robert D. C.
Winter, Christian
Donohoe, Timothy J.
author_sort Melikhova, Ekaterina Y.
collection PubMed
description The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling (for Trp‐2‐CO(2)H) and Blaise reaction (for Pyrr). An incorrect assignment of the pyrrolidinone stereochemistry of both compounds was confirmed by synthesizing epimers of the proposed structures. The spectroscopic data of these epimers were in complete agreement with those for the naturally derived material.
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spelling pubmed-51321532016-12-19 Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision Melikhova, Ekaterina Y. Pullin, Robert D. C. Winter, Christian Donohoe, Timothy J. Angew Chem Int Ed Engl Communications The total synthesis of dehydromicrosclerodermin B and microsclerodermin J is described. Efficient approaches to the unusual amino acids in the target molecules were developed on the basis of a Negishi coupling (for Trp‐2‐CO(2)H) and Blaise reaction (for Pyrr). An incorrect assignment of the pyrrolidinone stereochemistry of both compounds was confirmed by synthesizing epimers of the proposed structures. The spectroscopic data of these epimers were in complete agreement with those for the naturally derived material. John Wiley and Sons Inc. 2016-07-15 2016-08-08 /pmc/articles/PMC5132153/ /pubmed/27418203 http://dx.doi.org/10.1002/anie.201604764 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Melikhova, Ekaterina Y.
Pullin, Robert D. C.
Winter, Christian
Donohoe, Timothy J.
Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision
title Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision
title_full Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision
title_fullStr Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision
title_full_unstemmed Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision
title_short Dehydromicrosclerodermin B and Microsclerodermin J: Total Synthesis and Structural Revision
title_sort dehydromicrosclerodermin b and microsclerodermin j: total synthesis and structural revision
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5132153/
https://www.ncbi.nlm.nih.gov/pubmed/27418203
http://dx.doi.org/10.1002/anie.201604764
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AT winterchristian dehydromicroscleroderminbandmicroscleroderminjtotalsynthesisandstructuralrevision
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