Jump to main content
Jump to site search

Issue 40, 2017
Previous Article Next Article

Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium

Author affiliations

Abstract

The reaction of TMS-substituted epoxy alcohols (and derivatives) with dimsyl sodium (NaDMSO) to give 1-alkene-3,4-diols was used for the synthesis of enantiomerically enriched 17(R),18(S)-EpETE and two diastereoisomers of isoleukotoxin diol. In the synthesis of 17(R),18(S)-EpETE, the α-ethoxyethyl ether (EE) of the epoxy alcohol derived from (R)-1-TMS-1-penten-3-ol underwent reaction with NaDMSO to give the mono EE-protected 1-hexene-3,4-diol. The aldehyde obtained by hydroboration/oxidation was subjected to Wittig reaction to afford a mono EE-protected diol. The corresponding mono mesylate was prepared and subjected to epoxide ring formation to afford 17(R),18(S)-EpETE stereoselectively. Similarly, a reaction of the anti epoxy alcohol derived from (R)-1-TMS-1-octen-3-ol with NaDMSO gave the anti form of 1-nonene-3,4-diol, which was converted to 12(S),13(R)-isoleukotoxin diol through Wittig reaction. 12(R),13(R)-Isoleukotoxin diol was synthesized in a similar manner.

Graphical abstract: Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium

Back to tab navigation

Supplementary files

Publication details

The article was received on 13 Sep 2017, accepted on 29 Sep 2017 and first published on 29 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02291C
Citation: Org. Biomol. Chem., 2017,15, 8614-8626
  •   Request permissions

    Stereoselective synthesis of 17,18-epoxy derivative of EPA and stereoisomers of isoleukotoxin diol by ring opening of TMS-substituted epoxide with dimsyl sodium

    Y. Nanba, R. Shinohara, M. Morita and Y. Kobayashi, Org. Biomol. Chem., 2017, 15, 8614
    DOI: 10.1039/C7OB02291C

Search articles by author

Spotlight

Advertisements