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

Authors

Narihito Ogawa, Meiji University
Shinsaku Sone, Meiji University
Song Hong, LSU Health Sciences Center - New OrleansFollow
Yan Lu, LSU Health Sciences Center - New OrleansFollow
Yuichi Kobayashi, Meiji University

Document Type

Article

Publication Date

8-17-2020

Publication Title

Synlett

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.

First Page

1735

Last Page

1739

PubMed ID

35023886

Volume

31

Issue

17

Recommended Citation

Ogawa, Narihito; Sone, Shinsaku; Hong, Song; Lu, Yan; and Kobayashi, Yuichi, "Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid" (2020). School of Medicine Faculty Publications. 1603.
https://digitalscholar.lsuhsc.edu/som_facpubs/1603