Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps

[Image: see text] A new synthetic strategy to the ABCD ring system of the anticancer agent fredericamycin A (NSC-305263) was realized by the Diels–Alder reaction and olefin metathesis as key steps. The tactics developed here for the construction of the ABCD ring system also involve double Claisen re...

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Autores principales: Kotha, Sambasivarao, Cheekatla, Subba Rao, Fatma, Ambareen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6811863/
https://www.ncbi.nlm.nih.gov/pubmed/31656883
http://dx.doi.org/10.1021/acsomega.9b01178
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author Kotha, Sambasivarao
Cheekatla, Subba Rao
Fatma, Ambareen
author_facet Kotha, Sambasivarao
Cheekatla, Subba Rao
Fatma, Ambareen
author_sort Kotha, Sambasivarao
collection PubMed
description [Image: see text] A new synthetic strategy to the ABCD ring system of the anticancer agent fredericamycin A (NSC-305263) was realized by the Diels–Alder reaction and olefin metathesis as key steps. The tactics developed here for the construction of the ABCD ring system also involve double Claisen rearrangement followed by a retro-Diels–Alder reaction and ring-closing metathesis. The metathesis approach performs a key role in the construction of A and D rings of the ABCD core unit. More importantly, ABCD fragment synthesis was accomplished without the involvement of protecting groups.
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spelling pubmed-68118632019-10-25 Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps Kotha, Sambasivarao Cheekatla, Subba Rao Fatma, Ambareen ACS Omega [Image: see text] A new synthetic strategy to the ABCD ring system of the anticancer agent fredericamycin A (NSC-305263) was realized by the Diels–Alder reaction and olefin metathesis as key steps. The tactics developed here for the construction of the ABCD ring system also involve double Claisen rearrangement followed by a retro-Diels–Alder reaction and ring-closing metathesis. The metathesis approach performs a key role in the construction of A and D rings of the ABCD core unit. More importantly, ABCD fragment synthesis was accomplished without the involvement of protecting groups. American Chemical Society 2019-10-14 /pmc/articles/PMC6811863/ /pubmed/31656883 http://dx.doi.org/10.1021/acsomega.9b01178 Text en Copyright © 2019 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 Kotha, Sambasivarao
Cheekatla, Subba Rao
Fatma, Ambareen
Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
title Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
title_full Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
title_fullStr Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
title_full_unstemmed Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
title_short Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
title_sort synthetic approach to the abcd ring system of anticancer agent fredericamycin a via claisen rearrangement and ring-closing metathesis as key steps
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6811863/
https://www.ncbi.nlm.nih.gov/pubmed/31656883
http://dx.doi.org/10.1021/acsomega.9b01178
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