1428645-53-7Relevant academic research and scientific papers
Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol
Ferrer, Catalina,Fodran, Peter,Barroso, Santiago,Gibson, Robert,Hopmans, Ellen C.,Damste, Jaap Sinninghe,Schouten, Stefan,Minnaard, Adriaan J.
, p. 2482 - 2492 (2013/06/05)
An efficient asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol is presented employing catalytic asymmetric conjugate addition and catalytic epoxide ring opening as the key steps. Their occurrence in deep sea hydrothermal vents has been
Synthesis and analysis of the all-(S) side chain of phosphomycoketides: A test of NMR predictions for saturated oligoisoprenoid stereoisomers
Buter, Jeffrey,Yeh, Edmund A.-H.,Budavich, Owen W.,Damodaran, Krishnan,Minnaard, Adriaan J.,Curran, Dennis P.
, p. 4913 - 4918 (2013/07/05)
(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.
