3 years ago

Synthesis of Alfaprostol and PGF2α through 1,4-Addition of an Alkyne to an Enal Intermediate as the Key Step

Synthesis of Alfaprostol and PGF2α through 1,4-Addition of an Alkyne to an Enal Intermediate as the Key Step
Moritz J. Classen, Varinder K. Aggarwal, Hannah Baars
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03057

DOI: 10.1021/acs.orglett.7b03057

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