Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization

[Image: see text] The total synthesis of (±)-allocolchicine has been completed by employing cobalt-catalyzed alkyne [2 + 2 + 2]-cyclotrimerization as the key reaction. The essential diyne has been synthesized from easily available 3,4,5-trimethoxybenzaldehyde following simple chemical transformation...

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Autores principales: Paymode, Dinesh J., Ramana, Chepuri V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644368/
https://www.ncbi.nlm.nih.gov/pubmed/31457824
http://dx.doi.org/10.1021/acsomega.7b00980
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author Paymode, Dinesh J.
Ramana, Chepuri V.
author_facet Paymode, Dinesh J.
Ramana, Chepuri V.
author_sort Paymode, Dinesh J.
collection PubMed
description [Image: see text] The total synthesis of (±)-allocolchicine has been completed by employing cobalt-catalyzed alkyne [2 + 2 + 2]-cyclotrimerization as the key reaction. The essential diyne has been synthesized from easily available 3,4,5-trimethoxybenzaldehyde following simple chemical transformations. In general, the cycloaddition gave a mixture of C(9) and C(10) isomers thus allowing the synthesis of both allocolchicine and its C(10)-carboxylate. Because this cycloaddition was employed at the penultimate stage, it allowed the synthesis of various analogues having the diverse functionality at C(9) and/or C(10) of ring C.
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spelling pubmed-66443682019-08-27 Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization Paymode, Dinesh J. Ramana, Chepuri V. ACS Omega [Image: see text] The total synthesis of (±)-allocolchicine has been completed by employing cobalt-catalyzed alkyne [2 + 2 + 2]-cyclotrimerization as the key reaction. The essential diyne has been synthesized from easily available 3,4,5-trimethoxybenzaldehyde following simple chemical transformations. In general, the cycloaddition gave a mixture of C(9) and C(10) isomers thus allowing the synthesis of both allocolchicine and its C(10)-carboxylate. Because this cycloaddition was employed at the penultimate stage, it allowed the synthesis of various analogues having the diverse functionality at C(9) and/or C(10) of ring C. American Chemical Society 2017-09-08 /pmc/articles/PMC6644368/ /pubmed/31457824 http://dx.doi.org/10.1021/acsomega.7b00980 Text en Copyright © 2017 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 Paymode, Dinesh J.
Ramana, Chepuri V.
Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization
title Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization
title_full Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization
title_fullStr Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization
title_full_unstemmed Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization
title_short Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization
title_sort total synthesis of (±)-allocolchicine and its analogues using co-catalyzed alkyne [2 + 2 + 2]-cyclotrimerization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6644368/
https://www.ncbi.nlm.nih.gov/pubmed/31457824
http://dx.doi.org/10.1021/acsomega.7b00980
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