First total synthesis of the anti-inflammatory lipid mediator Resolvin D6
2011; Elsevier BV; Volume: 53; Issue: 1 Linguagem: Inglês
10.1016/j.tetlet.2011.11.003
ISSN1873-3581
AutoresAna R. Rodrı́guez, Bernd W. Spur,
Tópico(s)Eicosanoids and Hypertension Pharmacology
ResumoThe first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7–C14 fragment. Pd0/CuI Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.
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