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
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
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Basar, N | | | | Damodaran, K | | | | Liu, H | | | | Morris, GA | | | | Sirat, HM | | | | Thomas, EJ | | | | Curran, DP | curran@pitt.edu | CURRAN | |
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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: |
13 Jun 2021 00:55 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/25661 |
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