Total Synthesis of Δ 12 ‐Prostaglandin J 3 , a Highly Potent and Selective Antileukemic Agent

A catalytic asymmetric total synthesis of the potent and selective antileukemic Δ 12 ‐prostaglandin J 3 (Δ 12 ‐PGJ 3 ) is described. The convergent synthesis proceeded through intermediates 2 and 3 , formed enantioselectively from readily available starting materials and coupled through an aldol rea...

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Veröffentlicht in:Angewandte Chemie 2014-09, Vol.126 (39), p.10611-10615
Hauptverfasser: Nicolaou, K. C., Heretsch, Philipp, ElMarrouni, Abdelatif, Hale, Christopher R. H., Pulukuri, Kiran K., Kudva, Avinash K., Narayan, Vivek, Prabhu, K. Sandeep
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Sprache:ger
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Zusammenfassung:A catalytic asymmetric total synthesis of the potent and selective antileukemic Δ 12 ‐prostaglandin J 3 (Δ 12 ‐PGJ 3 ) is described. The convergent synthesis proceeded through intermediates 2 and 3 , formed enantioselectively from readily available starting materials and coupled through an aldol reaction followed by dehydration to afford stereoselectively the cyclopentenone alkylidene structural motif of the molecule.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201404917