Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan
Abstract A simple chemoenzymatic asymmetric route has been developed for the production of antimigraine agent ( R )‐Frovatriptan. Lipases and oxidoreductases have been identified as ideal biocatalysts for the production of enantiopure adequate synthetic intermediates under safe and environmentally f...
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crwiley:10.1002/ejoc.201300114 2024-06-02T07:57:09+00:00 Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan Busto, Eduardo Martínez‐Montero, Lía Gotor, Vicente Gotor‐Fernández, Vicente 2013 http://dx.doi.org/10.1002/ejoc.201300114 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201300114 http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.201300114/fullpdf en eng Wiley http://onlinelibrary.wiley.com/termsAndConditions#vor European Journal of Organic Chemistry volume 2013, issue 19, page 4057-4064 ISSN 1434-193X 1099-0690 journal-article 2013 crwiley https://doi.org/10.1002/ejoc.201300114 2024-05-03T10:35:37Z Abstract A simple chemoenzymatic asymmetric route has been developed for the production of antimigraine agent ( R )‐Frovatriptan. Lipases and oxidoreductases have been identified as ideal biocatalysts for the production of enantiopure adequate synthetic intermediates under safe and environmentally friendly conditions. ( S )‐3‐Hydroxy‐2,3,4,9‐tetrahydro‐1 H ‐carbazole‐6‐carbonitrile, an optimal building block for the synthesis of the drug, has been efficiently prepared through Candida antarctica lipase type B catalyzed acylation of its corresponding racemic mixture or alcohol dehydrogenase A mediated bioreduction of the corresponding ketone. The inversion of the chiral center has been identified as a key step, optimizing the process to avoid partial racemization. Finally, amine functionalization and nitrile hydrolysis have allowed the production of ( R )‐Frovatriptan in enantiomerically pure form. Article in Journal/Newspaper Antarc* Antarctica Wiley Online Library European Journal of Organic Chemistry 2013 19 4057 4064 |
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Open Polar |
collection |
Wiley Online Library |
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crwiley |
language |
English |
description |
Abstract A simple chemoenzymatic asymmetric route has been developed for the production of antimigraine agent ( R )‐Frovatriptan. Lipases and oxidoreductases have been identified as ideal biocatalysts for the production of enantiopure adequate synthetic intermediates under safe and environmentally friendly conditions. ( S )‐3‐Hydroxy‐2,3,4,9‐tetrahydro‐1 H ‐carbazole‐6‐carbonitrile, an optimal building block for the synthesis of the drug, has been efficiently prepared through Candida antarctica lipase type B catalyzed acylation of its corresponding racemic mixture or alcohol dehydrogenase A mediated bioreduction of the corresponding ketone. The inversion of the chiral center has been identified as a key step, optimizing the process to avoid partial racemization. Finally, amine functionalization and nitrile hydrolysis have allowed the production of ( R )‐Frovatriptan in enantiomerically pure form. |
format |
Article in Journal/Newspaper |
author |
Busto, Eduardo Martínez‐Montero, Lía Gotor, Vicente Gotor‐Fernández, Vicente |
spellingShingle |
Busto, Eduardo Martínez‐Montero, Lía Gotor, Vicente Gotor‐Fernández, Vicente Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan |
author_facet |
Busto, Eduardo Martínez‐Montero, Lía Gotor, Vicente Gotor‐Fernández, Vicente |
author_sort |
Busto, Eduardo |
title |
Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan |
title_short |
Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan |
title_full |
Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan |
title_fullStr |
Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan |
title_full_unstemmed |
Chemoenzymatic Asymmetric Synthesis of Serotonin Receptor Agonist ( R)‐Frovatriptan |
title_sort |
chemoenzymatic asymmetric synthesis of serotonin receptor agonist ( r)‐frovatriptan |
publisher |
Wiley |
publishDate |
2013 |
url |
http://dx.doi.org/10.1002/ejoc.201300114 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejoc.201300114 http://onlinelibrary.wiley.com/wol1/doi/10.1002/ejoc.201300114/fullpdf |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
European Journal of Organic Chemistry volume 2013, issue 19, page 4057-4064 ISSN 1434-193X 1099-0690 |
op_rights |
http://onlinelibrary.wiley.com/termsAndConditions#vor |
op_doi |
https://doi.org/10.1002/ejoc.201300114 |
container_title |
European Journal of Organic Chemistry |
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2013 |
container_issue |
19 |
container_start_page |
4057 |
op_container_end_page |
4064 |
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1800739229192421376 |