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A simple approach to 12-azaprostaglandin congeners

✍ Scribed by J. C. Lapierre Armande; U. K. Pandit

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
535 KB
Volume
99
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The base‐catalyzed 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‐(CH~2~)~6~C(OCH~3~)~3~. Subsequently, the α‐ and β‐(13,14‐dihydro)‐prostanoid chains were formed by sodium borohydride reduction, followed by hydrolysis. The resulting product, 1‐(3‐hydroxyoctyl)‐2‐(6‐methoxycarbonylhexyl)‐3‐pyrroline (13), constitutes a central intermediate for 12‐azaprostaglandins.

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