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Issue 25, 2013
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Total syntheses of oroidin, hymenidin and clathrodin

Sivappa Rasapalli,*a  Venkatreddy Kumbam,a  Abasaheb N. Dhawane,a  James A. Golen,a  Carl J. Lovelyb  and  Arnold L. Rheingoldc 
Author affiliations

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth, USA
E-mail: srasapalli@umassd.edu

b Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, USA

c Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, USA

Abstract

The total syntheses of oroidin, hymenidin and clathrodin are reported via the intermediacy of an imidazo[1,2-a]pyrimidine derivative. The chemistry described herein obviates the need for expensive guanidine reagents, multiply protected prefunctionalized 2-aminoimidazole synthons, or the need for laborious olefinations thereby achieving synthetic efficiency amenable to scale-up. The approach outlined in this manuscript provides an opportunity for further functionalizations through the imidazo[1,2-a]pyrimidine core and through functional groups placed strategically on the side chain.

Graphical abstract: Total syntheses of oroidin, hymenidin and clathrodin

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Publication details

The article was received on 04 Apr 2013, accepted on 07 May 2013 and first published on 10 May 2013


Article type: Communication
DOI: 10.1039/C3OB40668G
Citation: Org. Biomol. Chem., 2013,11, 4133-4137
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    Total syntheses of oroidin, hymenidin and clathrodin

    S. Rasapalli, V. Kumbam, A. N. Dhawane, J. A. Golen, C. J. Lovely and A. L. Rheingold, Org. Biomol. Chem., 2013, 11, 4133
    DOI: 10.1039/C3OB40668G

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