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

Hannah Baars, Moritz J. Classen, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

11 Citations (Scopus)
224 Downloads (Pure)

Abstract

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.

Original languageEnglish
Pages (from-to)6008-6011
Number of pages4
JournalOrganic Letters
Volume19
Issue number21
Early online date24 Oct 2017
DOIs
Publication statusPublished - 3 Nov 2017

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