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Molecules 2013, 18(9), 11485-11495; doi:10.3390/molecules180911485

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

1
Faculty of Specific Education, Zagazig University, Zagazig 44519, Egypt
2
Department of Chemistry and Biochemistry, Faculty of Science, Tabuk University, Tabuk PO Box 699, Saudi Arabia
3
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig 44519, Egypt
4
Department of Chemistry, Faculty of Science, Tanta University, Tanta 31527, Egypt
*
Author to whom correspondence should be addressed.
Received: 2 July 2013 / Revised: 30 July 2013 / Accepted: 26 August 2013 / Published: 16 September 2013
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Abstract

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. View Full-Text
Keywords: coumarins; dipyranocoumarin; dipetalolactone; Fremy’s salt coumarins; dipyranocoumarin; dipetalolactone; Fremy’s salt
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MDPI and ACS Style

Selim, Y.; Ouf, N.; Sakran, M. Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity. Molecules 2013, 18, 11485-11495.

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