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Synthesis and analysis of the all-(S) side chain of phosphomycoketides: A test of NMR predictions for saturated oligoisoprenoid stereoisomers

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
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Buter, J
Yeh, EAH
Budavich, OW
Damodaran, K
Minnaard, AJ
Curran, DPcurran@pitt.eduCURRAN
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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