eprintid: 25661
rev_number: 38
userid: 1418
dir: disk0/00/02/56/61
datestamp: 2015-07-17 20:04:30
lastmod: 2021-06-13 00:55:56
status_changed: 2015-07-17 20:04:30
type: article
metadata_visibility: show
item_issues_count: 0
eprint_status: archive
creators_name: Basar, N
creators_name: Damodaran, K
creators_name: Liu, H
creators_name: Morris, GA
creators_name: Sirat, HM
creators_name: Thomas, EJ
creators_name: Curran, DP
creators_email:
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creators_email: curran@pitt.edu
creators_id:
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creators_id: CURRAN
title: Systematic comparison of sets of 13C NMR spectra that are potentially identical. Confirmation of the configuration of a cuticular hydrocarbon from the cane beetle antitrogus parvulus
ispublished: pub
divisions: sch_as_chemistry
full_text_status: public
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.
date: 2014-08-15
date_type: published
publication: Journal of Organic Chemistry
volume: 79
number: 16
pagerange: 7477 - 7490
refereed: TRUE
issn: 0022-3263
id_number: 10.1021/jo5012027
other_id: NLM PMC4136713 [Available on 07/14/15]
pmcid: PMC4136713
pmid: 25019530
mesh_headings: Alkanes--chemical synthesis
mesh_headings: Alkanes--chemistry
mesh_headings: Animals
mesh_headings: Beetles--chemistry
mesh_headings: Biological Products--chemistry
mesh_headings: Hydrocarbons--chemical synthesis
mesh_headings: Hydrocarbons--chemistry
mesh_headings: Magnetic Resonance Spectroscopy
mesh_headings: Molecular Structure
mesh_headings: Stereoisomerism
chemical_names: 4,6,8,10,16,18-hexamethyldocosane
chemical_names: 4,6,8,10,16-pentamethyldocosane
chemical_names: Alkanes
chemical_names: Biological Products
chemical_names: Hydrocarbons
citation: 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 13C 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
document_url: http://d-scholarship-dev.library.pitt.edu/25661/1/licence.txt