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Issue 19, 2011
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Synthesis and configuration of the nonadecenetriol isolated from seeds of Persea americana

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Abstract

In an effort to establish the relative as well as absolute configuration of the trypanocidally active natural nonadec-6-en-1,2,4-triol isolated from Persea americana, the (2S,4R), (2S,4S), and (2R,4R) isomers were synthesized. The stereogenic centers taken from enantiopure chiral epoxy building blocks derived from inexpensive and readily available D-glucolactone. The (2R,4R) isomer gave 1H and 13C NMR as well as specific rotation in excellent consistence with those reported for the natural triol.

Graphical abstract: Synthesis and configuration of the nonadecenetriol isolated from seeds of Persea americana

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Publication details

The article was received on 04 Jun 2011, accepted on 04 Jul 2011 and first published on 11 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB05898C
Citation: Org. Biomol. Chem., 2011,9, 6797-6806
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    Synthesis and configuration of the nonadecenetriol isolated from seeds of Persea americana

    X. Yan, S. Zhang, Y. Wu and P. Gao, Org. Biomol. Chem., 2011, 9, 6797
    DOI: 10.1039/C1OB05898C

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