Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity

The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy’s salt-m...

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Autores principales: Selim, Yasser, Ouf, Nabil, Sakran, Mohamed
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269895/
https://www.ncbi.nlm.nih.gov/pubmed/24043143
http://dx.doi.org/10.3390/molecules180911485
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author Selim, Yasser
Ouf, Nabil
Sakran, Mohamed
author_facet Selim, Yasser
Ouf, Nabil
Sakran, Mohamed
author_sort Selim, Yasser
collection PubMed
description The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy’s salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line.
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spelling pubmed-62698952018-12-18 Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity Selim, Yasser Ouf, Nabil Sakran, Mohamed Molecules Article The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy’s salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line. MDPI 2013-09-16 /pmc/articles/PMC6269895/ /pubmed/24043143 http://dx.doi.org/10.3390/molecules180911485 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Selim, Yasser
Ouf, Nabil
Sakran, Mohamed
Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
title Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
title_full Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
title_fullStr Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
title_full_unstemmed Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
title_short Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity
title_sort fremy’s salt-mediated oxidative addition. a new approach in the total synthesis of naturally dipetalolactone and its immunomodulatory activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269895/
https://www.ncbi.nlm.nih.gov/pubmed/24043143
http://dx.doi.org/10.3390/molecules180911485
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AT sakranmohamed fremyssaltmediatedoxidativeadditionanewapproachinthetotalsynthesisofnaturallydipetalolactoneanditsimmunomodulatoryactivity

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