@article{pittir20657,
          volume = {78},
          number = {10},
           month = {May},
          author = {J Buter and EAH Yeh and OW Budavich and K Damodaran and AJ Minnaard and DP Curran},
           title = {Synthesis and analysis of the all-(S) side chain of phosphomycoketides: A test of NMR predictions for saturated oligoisoprenoid stereoisomers},
         journal = {Journal of Organic Chemistry},
           pages = {4913 -- 4918},
            year = {2013},
             url = {http://d-scholarship-dev.library.pitt.edu/20657/},
        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 ({$\sim$}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. {\copyright} 2013 American Chemical Society.}
}