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

Org Biomol Chem 2012 Mar 24;10(9):1743-5. Epub 2012 Jan 24.

Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia.

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. (13)C 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.

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http://dx.doi.org/10.1039/c2ob06906gDOI Listing
March 2012

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