Issue 40, 2017

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

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

Supplementary files

Article information

Article type
Paper
Submitted
13 Sep 2017
Accepted
29 Sep 2017
First published
29 Sep 2017

Org. Biomol. Chem., 2017,15, 8614-8626

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements