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

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

1,* , 2,3 and 2,4
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.
Keywords: coumarins; dipyranocoumarin; dipetalolactone; Fremy’s salt coumarins; dipyranocoumarin; dipetalolactone; Fremy’s salt
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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