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Fremy's salt-mediated oxidative addition. A new approach in the total synthesis of naturally dipetalolactone and its immunomodulatory activity
Journal article   Open access  Peer reviewed

Fremy's salt-mediated oxidative addition. A new approach in the total synthesis of naturally dipetalolactone and its immunomodulatory activity

Yasser Selim, Nabil Ouf and Mohamed Sakran
Molecules (Basel, Switzerland), Vol.18(9), pp.11485-11495
01/09/2013
DOI: https://doi.org/10.3390/molecules180911485
PMCID: PMC6269895
PMID: 24043143

Abstract

Acetylation Animals Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Cell Line, Tumor Chromones - chemical synthesis Chromones - pharmacology Cytotoxicity, Immunologic - drug effects Drug Screening Assays, Antitumor Female Immunologic Factors - chemical synthesis Immunologic Factors - pharmacology Killer Cells, Natural - drug effects Killer Cells, Natural - immunology Lethal Dose 50 Male Mice Mice, Inbred ICR Neoplasm Transplantation Nitroso Compounds - chemistry Oxidation-Reduction Tumor Burden - drug effects
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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https://doi.org/10.3390/molecules180911485View
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