Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

[Image: see text] The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8-endo-dig hydroarylation and a 6-exo-trig photoredox cyc...

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Autores principales: Miloserdov, Fedor M., Kirillova, Mariia S., Muratore, Michael E., Echavarren, Antonio M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5920919/
https://www.ncbi.nlm.nih.gov/pubmed/29432680
http://dx.doi.org/10.1021/jacs.7b13484
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author Miloserdov, Fedor M.
Kirillova, Mariia S.
Muratore, Michael E.
Echavarren, Antonio M.
author_facet Miloserdov, Fedor M.
Kirillova, Mariia S.
Muratore, Michael E.
Echavarren, Antonio M.
author_sort Miloserdov, Fedor M.
collection PubMed
description [Image: see text] The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8-endo-dig hydroarylation and a 6-exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided.
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spelling pubmed-59209192018-04-30 Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship Miloserdov, Fedor M. Kirillova, Mariia S. Muratore, Michael E. Echavarren, Antonio M. J Am Chem Soc [Image: see text] The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8-endo-dig hydroarylation and a 6-exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided. American Chemical Society 2018-02-12 2018-04-25 /pmc/articles/PMC5920919/ /pubmed/29432680 http://dx.doi.org/10.1021/jacs.7b13484 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Miloserdov, Fedor M.
Kirillova, Mariia S.
Muratore, Michael E.
Echavarren, Antonio M.
Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship
title Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship
title_full Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship
title_fullStr Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship
title_full_unstemmed Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship
title_short Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship
title_sort unified total synthesis of pyrroloazocine indole alkaloids sheds light on their biosynthetic relationship
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5920919/
https://www.ncbi.nlm.nih.gov/pubmed/29432680
http://dx.doi.org/10.1021/jacs.7b13484
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