Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B

A highly convergent strategy for the synthesis of the natural product (−)‐rubriflordilactone B, and the proposed structure of (−)‐pseudo‐rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodiu...

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Autores principales: Mohammad, Mujahid, Chintalapudi, Venkaiah, Carney, Jeffrey M., Mansfield, Steven J., Sanderson, Pollyanna, Christensen, Kirsten E., Anderson, Edward A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973266/
https://www.ncbi.nlm.nih.gov/pubmed/31595605
http://dx.doi.org/10.1002/anie.201908917
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author Mohammad, Mujahid
Chintalapudi, Venkaiah
Carney, Jeffrey M.
Mansfield, Steven J.
Sanderson, Pollyanna
Christensen, Kirsten E.
Anderson, Edward A.
author_facet Mohammad, Mujahid
Chintalapudi, Venkaiah
Carney, Jeffrey M.
Mansfield, Steven J.
Sanderson, Pollyanna
Christensen, Kirsten E.
Anderson, Edward A.
author_sort Mohammad, Mujahid
collection PubMed
description A highly convergent strategy for the synthesis of the natural product (−)‐rubriflordilactone B, and the proposed structure of (−)‐pseudo‐rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium‐catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo‐rubriflordilactone B and provides a robust platform for further synthetic and biological investigations.
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spelling pubmed-69732662020-01-27 Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B Mohammad, Mujahid Chintalapudi, Venkaiah Carney, Jeffrey M. Mansfield, Steven J. Sanderson, Pollyanna Christensen, Kirsten E. Anderson, Edward A. Angew Chem Int Ed Engl Communications A highly convergent strategy for the synthesis of the natural product (−)‐rubriflordilactone B, and the proposed structure of (−)‐pseudo‐rubriflordilactone B, is described. Late stage coupling of diynes containing the respective natural product FG rings with a common AB ring aldehyde precedes rhodium‐catalyzed [2+2+2] alkyne cyclotrimerization to form the natural product skeleton, with the syntheses completed in just one further operation. This work resolves the uncertainty surrounding the identity of pseudo‐rubriflordilactone B and provides a robust platform for further synthetic and biological investigations. John Wiley and Sons Inc. 2019-10-31 2019-12-09 /pmc/articles/PMC6973266/ /pubmed/31595605 http://dx.doi.org/10.1002/anie.201908917 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the 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
Mohammad, Mujahid
Chintalapudi, Venkaiah
Carney, Jeffrey M.
Mansfield, Steven J.
Sanderson, Pollyanna
Christensen, Kirsten E.
Anderson, Edward A.
Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B
title Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B
title_full Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B
title_fullStr Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B
title_full_unstemmed Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B
title_short Convergent Total Syntheses of (−)‐Rubriflordilactone B and (−)‐pseudo‐Rubriflordilactone B
title_sort convergent total syntheses of (−)‐rubriflordilactone b and (−)‐pseudo‐rubriflordilactone b
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6973266/
https://www.ncbi.nlm.nih.gov/pubmed/31595605
http://dx.doi.org/10.1002/anie.201908917
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