74850-97-8Relevant academic research and scientific papers
A simple approach to 12-azaprostaglandin congeners
Armande, J. C. Lapierre,Pandit, U. K.
, p. 87 - 91 (2007/10/02)
The base-catalysed alkylation of N-acylated 3-pyrrolines has been studied.The reaction has been utilized in an approach to the synthesis of 12-azaprostaglandins according to the following sequence. 3-Pyrroline was acylated with 1-chloro-1-octen-3-one and the resulting amide alkylated at the 2-position with I-(CH2)6C(OCH3)3.Subsequently, the α- and β-(13,14-dihydro)-prostanoid chains were formed by sodium borohyride reduction, followed by hydrolysis.The resulting product, 1-(3-hydroxyoctyl)-2-(6-methoxycarbonylhexyl)-3-pyrroline (13), constitutes a central intermediate for 12-azaprostaglandins.
