Prostaglandin Total Synthesis Enabled by the Organocatalytic Dimerization of Succinaldehyde

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Abstract

Prostaglandins have been attractive targets in total synthesis for over 50 years, resulting in the development of new synthetic strategies and methodologies that have served the broader chemical community. However, these molecules are not just of academic interest, a number of prostaglandin analogues are used in the clinic, and some are even on the WHO list of essential medicines. In this personal account, we describe our own approach to the family of prostaglandins, which centers around the synthesis of a key enal intermediate, formed from the l ‐proline catalysed dimerization of succinaldehyde. We highlight the discovery and further optimization of this key reaction, its scale up, and subsequent application to a range of prostaglandins.
Original languageEnglish
Number of pages13
JournalChemical Record
Early online date16 Jul 2020
DOIs
Publication statusE-pub ahead of print - 16 Jul 2020

Keywords

  • prostaglandins
  • total synthesis
  • organocatalysis
  • aldol reaction
  • asymmetric synthesis

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