Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core

[Image: see text] Two different approaches funded upon the intramolecular [4 + 2]-cycloaddition of in situ generated o-quinone methides have been explored to construct the central tetracyclic core of parvifolals A/B. At the outset, a cross-pinacol coupling of 2-formyl tri-O-methyl resveratrol with 4...

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Autores principales: Paymode, Dinesh J., Ramana, Chepuri V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648467/
https://www.ncbi.nlm.nih.gov/pubmed/31459360
http://dx.doi.org/10.1021/acsomega.8b02777
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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] Two different approaches funded upon the intramolecular [4 + 2]-cycloaddition of in situ generated o-quinone methides have been explored to construct the central tetracyclic core of parvifolals A/B. At the outset, a cross-pinacol coupling of 2-formyl tri-O-methyl resveratrol with 4-methoxysalicylaldehyde followed by acid treatment was found to provide the desired tetracyclic core with an internal olefin. The requisite pendant aryl group has been introduced by a Pd-catalyzed direct coupling of corresponding diazonium salt.
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spelling pubmed-66484672019-08-27 Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core Paymode, Dinesh J. Ramana, Chepuri V. ACS Omega [Image: see text] Two different approaches funded upon the intramolecular [4 + 2]-cycloaddition of in situ generated o-quinone methides have been explored to construct the central tetracyclic core of parvifolals A/B. At the outset, a cross-pinacol coupling of 2-formyl tri-O-methyl resveratrol with 4-methoxysalicylaldehyde followed by acid treatment was found to provide the desired tetracyclic core with an internal olefin. The requisite pendant aryl group has been introduced by a Pd-catalyzed direct coupling of corresponding diazonium salt. American Chemical Society 2019-01-10 /pmc/articles/PMC6648467/ /pubmed/31459360 http://dx.doi.org/10.1021/acsomega.8b02777 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 Paymode, Dinesh J.
Ramana, Chepuri V.
Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core
title Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core
title_full Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core
title_fullStr Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core
title_full_unstemmed Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core
title_short Studies toward the Total Synthesis of Parvifolals A/B: An Intramolecular o-Quinone Methide [4 + 2]-Cycloaddition To Construct the Central Tetracyclic Core
title_sort studies toward the total synthesis of parvifolals a/b: an intramolecular o-quinone methide [4 + 2]-cycloaddition to construct the central tetracyclic core
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648467/
https://www.ncbi.nlm.nih.gov/pubmed/31459360
http://dx.doi.org/10.1021/acsomega.8b02777
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