First total synthesis of the anti-inflammatory and pro-resolving lipid mediator 16(R),17(S)-diHDHA

Ana R. Rodriguez, Bernd W. Spur

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

The first total synthesis of the anti-inflammatory and pro-resolving lipid mediator 16(R),17(S)-diHDHA, derived from docosahexaenoic acid (DHA), and its 16-epimer have been achieved. Two synthetic approaches are described for the synthesis of 16(R),17(S)-diHDHA. The first strategy started from DHA and used an enzymatic reaction, a vanadium catalyzed allylic epoxidation and a base-promoted epoxide isomerization. The second approach utilized a chiral pool strategy starting from 2-deoxy-D-ribose to establish the chiral centers; Wittig reactions, mild acetonide cleavage and ester hydrolysis were the key steps in the synthesis.

Original languageEnglish (US)
Pages (from-to)1143-1146
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number12
DOIs
StatePublished - Mar 21 2018

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'First total synthesis of the anti-inflammatory and pro-resolving lipid mediator 16(R),17(S)-diHDHA'. Together they form a unique fingerprint.

Cite this