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Total Synthesis of Δ 12 ‐Prostaglandin J 3 , a Highly Potent and Selective Antileukemic Agent
Author(s) -
Nicolaou K. C.,
Heretsch Philipp,
ElMarrouni Abdelatif,
Hale Christopher R. H.,
Pulukuri Kiran K.,
Kudva Avinash K.,
Narayan Vivek,
Prabhu K. Sandeep
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201404917
Subject(s) - cyclopentenone , total synthesis , aldol reaction , chemistry , stereochemistry , prostaglandin , molecule , aldol condensation , enantioselective synthesis , combinatorial chemistry , catalysis , organic chemistry , biochemistry
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.