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. 2013 Sep 16;18(9):11485-95.
doi: 10.3390/molecules180911485.

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

Yasser Selim  1 , Nabil Ouf, Mohamed Sakran
Affiliations

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

Yasser Selim et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
Total synthesis of natural dipetalolactone.
See this image and copyright information in PMC

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References

    1. Robert D., Murray H. The Naturally Occurring Coumarins. Volume 38. Fortschitte Der Chemie Organischer Naturstoffe; Glasgow, UK: 2002. pp. 1–619. - PubMed
    1. Kiran D.P., Swati P.J., Sunil R.B., Shubhada R.T. Pattern of anti-HIV dipyranocoumarin expression in callus cultures of Calophyllum inophyllum Linn. J. Biotechnol. 2007;130:346–353. doi: 10.1016/j.jbiotec.2007.04.024. - DOI - PubMed
    1. Murray R.D.H., Méndez J., Brown S.A. Chemistry and Biochemistry. John Wiley & Sons Ltd; New York, NY, USA: 1982. The Natural Coumarins. Occurrence; pp. 343–345.
    1. Ribeiro C.V.C., Kaplan M.A.C. Evolutionary families of trends producers coumarins in angiosperms. Quim. Nova. 2002;25:533–538. doi: 10.1590/S0100-40422002000400004. - DOI
    1. Melo M.F.F., Zickel C.S. Genres zanthoxylum L. and Esenbeckia Kunth (Rutaceae) in the State of Pernambuco, Brazil. Acta Bot. Bras. 2004;18:73–90.

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