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Synthesis of Alfaprostol and PGF through 1,4-Addition of an Alkyne to an Enal Intermediate as the Key Step

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journal contribution
posted on 24.10.2017, 18:06 authored by Hannah Baars, Moritz J. Classen, Varinder K. Aggarwal
The veterinary drug Alfaprostol and prostaglandin PGF have been synthesized in just nine steps. The strategy involved the conjugate addition of an alkyne to a bicyclic enal, available in three steps by a proline-catalyzed aldol reaction of succinaldehyde. In the case of Alfaprostol, this resulted in the shortest synthesis reported to date. For PGF, this approach improved our previous route by making the 1,4-addition and ozonolysis more operationally simple.