Prostanoid biosynthesis

Epoxide ring-opening with transfer of an sp carbon moiety was applied in a short synthesis [44] of eicosanoid 56 [45], relevant in marine prostanoid biosynthesis (Scheme 9.13). Homoallyl alcohol 55 was obtained in good yield from 54 by use of a cyano-Gilman alkenylcuprate [46]. 

Minghetti L, Levi G (1995) Induction of prostanoid biosynthesis by bacterial lipopolysaccharide and isoproterenol in rat microglial cultures. J. Neurochem. 65 2690-2698. 

Conversion of arachidonate to PGH via cyclooxygenase catalysis is a key regnlatory step in prostanoid biosynthesis. 

Although PLAj activity is the first step for prostanoid biosynthesis and can limit their availability, it is not the rate-limiting step in prostanoid formation. However, direct inhibition of PLA could potentially block the production of all eicosanoids, making it a desirable target for pharmacological intervention (Yedgar et al., 2000). 

Fig. 4.7. Hypothetical model for the regulation of prostanoid biosynthesis in normal and inflammatory states. Based on results published in ref 40.

Corey, E.J. and Matsuda, S.P.T. (1987) Generality of marine prostanoid biosynthesis by the 2-oxidopentadienyl cation pathway. Tetrahedron Lett., 28,4247-4250. 

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