[Synthesis of the leukotriene A4 methyl ester via acetylene intermediates].
The strategy of acyclic eicosanoid synthesis via polyacetylenic intermediates is examplified by the synthesis of the racemic leukotriene A4 methyl ester. Leukotriene synthons, namely, trideca-1,4,7-triyne and methyl 6-formyl-5,6-trans-epoxyhexanoate, were synthesised using propargylic alcohol (thrice) and 1-heptyne as starting materials. In the course of the synthesis all new carbon-carbon bonds were created through acetylenide anion condensations and (Z)-double bonds are introduced by triple bond hydrogenations. The strategy provides a straightforward and stereospecific synthetic pathway.
Belosludtsev
Iu Iu
IuIu
Miagkova
G I
GI
Evstigneeva
R P
RP
Bobrova
N I
NI
Pivnitskiĭ
K K
KK
D000114:Acetylene; D001095:Arachidonic Acids / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D017572:Leukotriene A4 / Q000031:analogs & derivatives
D001095:Arachidonic Acids; D017572:Leukotriene A4; C043073:leukotriene A methyl ester; D000114:Acetylene
Sintez metilovogo éfira leĭkotriena A4 na osnove atsetilenovykh soedineniĭ.