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Rapid, inexpensive gram-scale synthesis of prostaglandins

A method for synthesizing prostaglandins could help generate new compounds using fewer manufacturing steps. Synthesis of prostaglandin analogs is complicated, and drugs such as Xalatan latanoprost are still manufactured via a 20-step process. A two-step reaction sequence from inexpensive starting materials produced gram-scale quantities of a bicyclic enal intermediate. A five-step reaction sequence converted the enal intermediate to gram-scale quantities of prostaglandin F2a (PGF2a). Ongoing work includes testing the biological activity of compound libraries generated from the enal intermediate.
Xalatan, a prostaglandin F receptor (PTGFR) agonist from Pfizer Inc., is marketed to decrease intraocular pressure in glaucoma.
At least 11 companies market prostaglandins or prostaglandin analogs to treat cardiovascular, ophthalmic, genitourinary and gastrointestinal diseases.

SciBX 5(33); doi:10.1038/scibx.2012.879
Published online Aug. 23, 2012

Patented; available for licensing

Coulthard, G. et al. Nature;

published online Aug. 15, 2012;
Contact: Varinder K. Aggarwal,

University of Bristol, Bristol, U.K.