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Issue 9, 2012
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Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry

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Abstract

The stereoselective reaction of an allyl bromide with an aldehyde mediated by a low valency bismuth species was the key reaction in stereoselective syntheses of (4S,6R,8R,10S,16S)- and (4S,6R,8R,10S,16R)-4,6,8,10,16-pentamethyldocosanes. 13C NMR data for these compounds confirmed that the cuticular hydrocarbon isolated from the cane beetle Antitrogus parvulus was the (4S,6R,8R,10S,16S)-stereoisomer.

Graphical abstract: Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry

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Publication details

The article was received on 11 Nov 2011, accepted on 16 Dec 2011 and first published on 20 Dec 2011


Article type: Communication
DOI: 10.1039/C2OB06906G
Org. Biomol. Chem., 2012,10, 1743-1745

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    Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry

    N. B. Basar, H. Liu, D. Negi, H. M. Sirat, G. A. Morris and E. J. Thomas, Org. Biomol. Chem., 2012, 10, 1743
    DOI: 10.1039/C2OB06906G

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