Buter, J and Yeh, EAH and Budavich, OW and Damodaran, K and Minnaard, AJ and Curran, DP
(2013)
Synthesis and analysis of the all-(S) side chain of phosphomycoketides: A test of NMR predictions for saturated oligoisoprenoid stereoisomers.
Journal of Organic Chemistry, 78 (10).
4913 - 4918.
ISSN 0022-3263
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Abstract
(4S,8S,12S,16S,20S)-Pentamethylheptacosan-1-ol has been synthesized and analyzed by resolution-enhanced NMR spectroscopy with the aid of a recent set predicted spectra of all its stereoisomers. The configuration was confirmed, but isomer purity of the sample (∼70%) was lower than expected. A truncated analogue, (2S,6S,10S,14S)-2,6,10,14-tetramethylhenicosan-1-ol TBDPS ether, was prepared from a late stage synthetic intermediate. Analysis of its spectra confirmed the configuration and showed that the sample was isomerically pure. The results suggest that a late-stage epimerization, not a failure of an asymmetric synthesis step, caused the formation of minor stereoisomers in the sample of pentamethylheptacosan-1-ol. The study shows the value of the predicted set of oligoisoprenoid spectra and further extends the predictive model to a new subclass of compounds. © 2013 American Chemical Society.
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Details
Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID  |
---|
Buter, J | | | | Yeh, EAH | | | | Budavich, OW | | | | Damodaran, K | | | | Minnaard, AJ | | | | Curran, DP | curran@pitt.edu | CURRAN | |
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Date: |
17 May 2013 |
Date Type: |
Publication |
Journal or Publication Title: |
Journal of Organic Chemistry |
Volume: |
78 |
Number: |
10 |
Page Range: |
4913 - 4918 |
DOI or Unique Handle: |
10.1021/jo4005298 |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
0022-3263 |
MeSH Headings: |
Fatty Alcohols--analysis; Fatty Alcohols--chemical synthesis; Fatty Alcohols--chemistry; Magnetic Resonance Spectroscopy; Molecular Structure; Stereoisomerism; Terpenes--chemistry |
Other ID: |
NLM NIHMS471157 [Available on 05/17/14], NLM PMC3714862 [Available on 05/17/14] |
PubMed Central ID: |
PMC3714862 |
PubMed ID: |
23582013 |
Date Deposited: |
28 Feb 2014 20:11 |
Last Modified: |
02 Feb 2019 15:58 |
URI: |
http://d-scholarship.pitt.edu/id/eprint/20657 |
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