Synthesis of 8-azaprostaglandin E1 and E2

A Formal Synthesis of (−)-Paroxetine by Enantioselective Ring Enlargement of a Trisubstituted Prolinol

“…Compound (+)‐ 3 was synthesized in three steps from L ‐pyroglutamic acid ( 1 ) 49. After treatment of L ‐pyroglutamic acid with thionyl chloride in methanol (88% yield), the corresponding methyl ester was reduced with NaBH 4 (EtOH, 0 °C to room temp., yield = 90%) and the amidoalcohol (+)‐ 2 50 was protected with benzaldehyde in the presence of a catalytic amount of p ‐toluenesulfonic acid (TsOH). The optically pure bicyclic compound (+)‐ 3 was isolated in 69% yield ([α] D 20 = +237, c = 1.2, CHCl 3 ) (Scheme ).…”

Synthesis of 14-Hydroxy-8-Azaprostanoic Acids Methyl Ester

“…Any substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing, systematic supply, or distribution in any form to anyone is expressly forbidden. Terms & Conditions of access and use can be found at http:// www.tandfonline.com/page/terms-and-conditions ( 3 ) to give an 85% yield of ( 5 ) or on I-octene (2) to produce a 92% yield of the isoxazoline (4) easily converted to (5) by means of I( -manganese dioxide . 10 Reductive ring opening of (6) at atmospheric pressure in the presence of Pt02 in methanol proceeded with formation of the enaminoketoacid ( 7 ) , which was then cyclized by treatment with ethyl chlorocarbonate in THF solution at 00 in the 219 Copyright 0 1 9 7 8 by Marcel Dekker, Inc All Rights Reserved.…”

Difluoromethylene at the γ-Lactam α-Position Improves 11-Deoxy-8-aza-PGE1 Series EP4 Receptor Binding and Activity: 11-Deoxy-10,10-difluoro-8-aza-PGE1 Analog (KMN-159) as a Potent EP4 Agonist

“…The 2-pyrrolidinone (γ-lactam, or E ring) scaffold is a known synthetic PGE structural mimic deployed in EP receptor-based structure activity relationship (SAR) programs for decades (Figure ). − The relative ease with which a diverse array of α- and ω-chains can be introduced on the core ring makes this an attractive template from a synthetic enablement perspective.…”