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

Basar, N and Damodaran, K and Liu, H and Morris, GA and Sirat, HM and Thomas, EJ and Curran, DP (2014) Systematic comparison of sets of <sup>13</sup>C 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). 7477 - 7490. ISSN 0022-3263

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Abstract

A systematic process is introduced to compare 13C 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 13C 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). © 2014 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Basar, N
Damodaran, K
Liu, H
Morris, GA
Sirat, HM
Thomas, EJ
Curran, DPcurran@pitt.eduCURRAN
Date: 15 August 2014
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 79
Number: 16
Page Range: 7477 - 7490
DOI or Unique Handle: 10.1021/jo5012027
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Alkanes--chemical synthesis; Alkanes--chemistry; Animals; Beetles--chemistry; Biological Products--chemistry; Hydrocarbons--chemical synthesis; Hydrocarbons--chemistry; Magnetic Resonance Spectroscopy; Molecular Structure; Stereoisomerism
Other ID: NLM PMC4136713 [Available on 07/14/15]
PubMed Central ID: PMC4136713
PubMed ID: 25019530
Date Deposited: 17 Jul 2015 20:04
Last Modified: 22 Jun 2021 13:56
URI: http://d-scholarship.pitt.edu/id/eprint/25661

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