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. © 2012 The Royal Society of Chemistry.
CITATION STYLE
Basar, N. B., Liu, H., Negi, D., Sirat, H. M., Morris, G. A., & Thomas, E. J. (2012). Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: Confirmation of the relative stereochemistry. Organic and Biomolecular Chemistry, 10(9), 1743–1745. https://doi.org/10.1039/c2ob06906g
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