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Synlett 2020; 31(17): 1735-1739
DOI: 10.1055/s-0040-1706415
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid

Narihito Ogawa∗
a   Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan   Email: narihito@meiji.ac.jp
,
Shinsaku Sone
a   Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan   Email: narihito@meiji.ac.jp
,
Song Hong
b   Neuroscience Center of Excellence, Louisiana State University, Health Sciences Center, 2020 Gravier St., New Orleans, LA 70112, USA
c   Department of Ophthalmology, Louisiana State University, Health Sciences Center, New Orleans, LA 70112, USA
,
Yan Lu
b   Neuroscience Center of Excellence, Louisiana State University, Health Sciences Center, 2020 Gravier St., New Orleans, LA 70112, USA
,
Yuichi Kobayashi
d   Meiji University, Organization for the Strategic Coordination of Research and Intellectual Properties, 1-1-1 Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan
› Author AffiliationsThis work was supported by the Japan Society for the Promotion of Science (JSPS KAKENHI, Grant Number JP15H05904 (Y. K.)). This work was also supported by the National Institute of Health of The United States of America (Grant Numbers R01DK087800-07, R01DK087800-07S1, 1R21AG060430, 1R21AG060430S1, 1R21AG066119, and R01GM136874 (S. H.)).
Further Information

Publication History

Received: 29 June 2020

Accepted after revision: 16 July 2020

Publication Date:
17 August 2020 (online)

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Abstract

The C16–C22 fragment with the acetylene terminus was constructed through the asymmetric dihydroxylation of the corresponding olefin, while the 15-iodo-olefin corresponding to the C11–C15 part was prepared via the asymmetric transfer hydrogenation of the corresponding acetylene ketone followed by hydrozirconation/iodination. Both pieces were joined by a Sonogashira coupling, and the product was further converted into the title compound via a Wittig reaction with the remaining C1–C10 segment and Boland reduction using Zn with TMSCl.

Key words

DHA metabolite - trihydroxylated DHA - organic synthesis - enyne - Boland reduction - TMSCl - Hansen protocol

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706415.
  • Supporting Information
 

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