Total Synthesis of Δ12-Prostaglandin J3

Total Synthesis of Δ12-Prostaglandin J3

Author: Veronika Belusa

Δ12-prostaglandin J312-PGJ3) is a potent and selective antileukemic. It is of great interest to get Δ12-PGJ3 readily available for thorough biological and pharmacological investigations. This would open the way for analogue design, synthesis, and biological evaluation of this important ω-3 series of eicosanoids.

K. C. Nicolaou, Rice University, Houston, TX, USA, and colleagues have described a catalytic asymmetric total synthesis of Δ12-PGJ3 in 92 % yield. They started from readily available starting materials. A convergent synthesis proceeded through two advanced cyclopentenone and aldehyde intermediates. To stereoselectively achieve the cyclopentenone alkylidene structural motif of the prostaglandin, coupling through an aldol reaction was followed by dehydration.

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