Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity

[Image: see text] An enantioselective total synthesis of spliceostatin E has been accomplished. The δ-lactone unit A was constructed from readily available (R)-glycidyl alcohol using a ring-closing olefin metathesis as the key reaction. A cross-metathesis of ring A containing δ-lactone and the funct...

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Autores principales: Ghosh, Arun K., Veitschegger, Anne M., Sheri, Venkata Reddy, Effenberger, Kerstin A., Prichard, Beth E., Jurica, Melissa S.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4260646/
https://www.ncbi.nlm.nih.gov/pubmed/25423085
http://dx.doi.org/10.1021/ol503127r
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author Ghosh, Arun K.
Veitschegger, Anne M.
Sheri, Venkata Reddy
Effenberger, Kerstin A.
Prichard, Beth E.
Jurica, Melissa S.
author_facet Ghosh, Arun K.
Veitschegger, Anne M.
Sheri, Venkata Reddy
Effenberger, Kerstin A.
Prichard, Beth E.
Jurica, Melissa S.
author_sort Ghosh, Arun K.
collection PubMed
description [Image: see text] An enantioselective total synthesis of spliceostatin E has been accomplished. The δ-lactone unit A was constructed from readily available (R)-glycidyl alcohol using a ring-closing olefin metathesis as the key reaction. A cross-metathesis of ring A containing δ-lactone and the functionalized tetrahydropyran B-ring provided spliceostatin E. Our biological evaluation of synthetic spliceostatin E revealed that it does not inhibit splicing in vitro and does not impact speckle morphology in cells. Spliceostatin E was reported to possess potent antitumor activity.
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spelling pubmed-42606462015-11-25 Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity Ghosh, Arun K. Veitschegger, Anne M. Sheri, Venkata Reddy Effenberger, Kerstin A. Prichard, Beth E. Jurica, Melissa S. Org Lett [Image: see text] An enantioselective total synthesis of spliceostatin E has been accomplished. The δ-lactone unit A was constructed from readily available (R)-glycidyl alcohol using a ring-closing olefin metathesis as the key reaction. A cross-metathesis of ring A containing δ-lactone and the functionalized tetrahydropyran B-ring provided spliceostatin E. Our biological evaluation of synthetic spliceostatin E revealed that it does not inhibit splicing in vitro and does not impact speckle morphology in cells. Spliceostatin E was reported to possess potent antitumor activity. American Chemical Society 2014-11-25 2014-12-05 /pmc/articles/PMC4260646/ /pubmed/25423085 http://dx.doi.org/10.1021/ol503127r Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Ghosh, Arun K.
Veitschegger, Anne M.
Sheri, Venkata Reddy
Effenberger, Kerstin A.
Prichard, Beth E.
Jurica, Melissa S.
Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity
title Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity
title_full Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity
title_fullStr Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity
title_full_unstemmed Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity
title_short Enantioselective Synthesis of Spliceostatin E and Evaluation of Biological Activity
title_sort enantioselective synthesis of spliceostatin e and evaluation of biological activity
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4260646/
https://www.ncbi.nlm.nih.gov/pubmed/25423085
http://dx.doi.org/10.1021/ol503127r
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