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 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; in revised form: 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

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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.

AMA 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(9):11485-11495.

Chicago/Turabian Style

Selim, Yasser; Ouf, Nabil; Sakran, Mohamed. 2013. "Fremy’s Salt-Mediated Oxidative Addition. A New Approach in the Total Synthesis of Naturally Dipetalolactone and Its Immunomodulatory Activity." Molecules 18, no. 9: 11485-11495.

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