Reaction of 1-Trimethylsilyl-1,2-epoxy-3-alkanols with Alkynes and Application to the Synthesis of 18-HEPE-Reference-Cited by-同舟云学术

Reaction of 1-Trimethylsilyl-1,2-epoxy-3-alkanols with Alkynes and Application to the Synthesis of 18-HEPE

Published:2018-06-29 Issue:13 Volume:29 Page:1791-1795
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Kobayashi Yuichi¹,Nanba Yutaro¹,Morita Masao¹

Affiliation:

1. Department of Bioengineering, Tokyo Institute of Technology

Abstract

A reaction of epoxy alcohols (anti and/or syn isomers) derived from (E)-TMS-CH=CHCH(OH)R with TMS-C≡CLi in THF/HMPA stereoselectively afforded (E)-TMS-C≡C-CH=CHCH(OH)R. The (E) stereochemistry was independent of the anti/syn stereochemistry, but the syn isomers showed higher reactivity than the anti isomers. The reaction was applied to the synthesis of (18R)- and (18S)-HEPE.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0037-1610194.pdf

Cited by 7 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Stereoselective Syntheses of Polyunsaturated Fatty Acids, 13-(S)-HODE and 15-(S)-HETE;The Journal of Organic Chemistry;2024-08-03

2. Stereoselective Synthesis, Configurational Assignment and Biological Evaluations of the Lipid Mediator RvD2 n‐3 DPA;Chemistry – A European Journal;2021-12-28

3. Stereoselective syntheses and biological activities of E-series resolvins;Organic & Biomolecular Chemistry;2021

4. Synthesis of Resolvin D6 and the Silyl Ether of the Resolvin E2 Methyl Ester via trans-Enynyl Alcohols;Synlett;2019-05-10

5. The Hudrlik–Peterson Reaction of Secondary cis-TMS-Epoxy Alcohols and its Application to the Synthesis of the Fatty Acid Intermediates;Synlett;2019-04-16