An efficient total synthesis of leukotriene B4

Lipid mediators have attracted great interest from scientists within the chemical, medicinal, and pharmaceutical research community. One such example is leukotriene B-4 which has been the subject of many pharmacological studies. Herein, we report a convergent and stereoselective synthesis of this po...

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Published inOrganic & biomolecular chemistry Vol. 13; no. 19; pp. 5412 - 5417
Main Authors Primdahl, Karoline Gangestad, Tungen, Jorn Eivind, Aursnes, Marius, Hansen, Trond Vidar, Vik, Anders
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.05.2015
Subjects
Aldehydes - chemical synthesis
Aldehydes - chemistry
Alkynes - chemical synthesis
Alkynes - chemistry
Chemistry
Chemistry, Organic
Leukotriene B4 - biosynthesis
Leukotriene B4 - chemical synthesis
Leukotriene B4 - chemistry
Physical Sciences
Science & Technology
LIPID MEDIATOR
POLYMORPHONUCLEAR LEUKOCYTES
CONJUGATE REDUCTION
PROPARGYLIC ALCOHOLS
ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
OMEGA-OXIDATION
ARACHIDONIC-ACID
PROTECTIN D1
REDUCTIVE ELIMINATION
HYDRIDE
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Summary:Lipid mediators have attracted great interest from scientists within the chemical, medicinal, and pharmaceutical research community. One such example is leukotriene B-4 which has been the subject of many pharmacological studies. Herein, we report a convergent and stereoselective synthesis of this potent lipid mediator in 5% yield over 10 steps in the longest linear sequence from commercial starting materials. The key steps were a stereocontrolled acetate-aldol reaction with Nagao's chiral auxiliary and a Z-selective Boland reduction. All spectroscopic data were in agreement with those previously reported.
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ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00473j