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Systematic comparison of sets of C-13 NMR spectra that are potentially identical. Confirmation of the configuration of a cuticular hydrocarbon from the cane beetle antitrogus parvulus

Basar, Norazah and Damodaran, Krishnan and Liu, Hao and Morris, Gareth A. and Sirat, Hasnah M. and Thomas, Eric J. and Curran, Dennis P. (2014) Systematic comparison of sets of C-13 NMR spectra that are potentially identical. Confirmation of the configuration of a cuticular hydrocarbon from the cane beetle antitrogus parvulus. Journal of Organic Chemistry, 79 (16). pp. 7477-7490. ISSN 0022-3263

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Official URL: http://dx.doi.org/10.1021/jo5012027

Abstract

A systematic process is introduced to compare C-13 NMR spectra of two (or more) candidate samples of known structure to a natural product sample of unknown structure. The process is designed for the case where the spectra involved can reasonably be expected to be very similar, perhaps even identical. It is first validated by using published C-13 NMR data sets for the natural product 4,6,8,10,16,18-hexamethyldocosane. Then the stereoselective total syntheses of two candidate isomers of the related 4,6,8,10,16-pentamethyldocosane natural product are described, and the process is applied to confidently assign the configuration of the natural product as (4S,6R,8R,10S,16S). This is accomplished even though the chemical shift differences between this isomer and its (16R)-epimer are only +/- 5-10 ppb (+/- 0.005-0.01 ppm).

Item Type:Article
Uncontrolled Keywords:absolute-configuration, metallic bismuth
Subjects:Q Science
Divisions:Science
ID Code:62802
Deposited By: Fazli Masari
Deposited On:18 Jun 2017 08:01
Last Modified:18 Jun 2017 08:01

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