Issue 9, 2012
From the journal:

Organic & Biomolecular Chemistry

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

Norazah B. Basar,a   Hao Liu,b   Devendra Negi,c   Hasnah M. Sirat,a   Gareth A. Morrisb  and  Eric J. Thomas*b  

* Corresponding authors

a Universiti Teknologi Malaysia, 81310 Skudai, Johor, Malaysia

b School of Chemistry, University of Manchester, Manchester, UK
E-mail: e.j.thomas@manchester.ac.uk
Fax: +44 (0)161 275 4939
Tel: +44 (0)161 275 4614

c Department of Chemistry, HNB Garhwal University (A Central University), Srinagar (Garhwal), Uttarakhand, India

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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Article information

DOI
https://doi.org/10.1039/C2OB06906G
Article type
Communication
Submitted
11 Nov 2011
Accepted
16 Dec 2011
First published
20 Dec 2011

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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