18. Total Synthesis of Δ12-Prostaglandin J3, a Highly Potent and Selective Antileukemic Agent

K.C. Nicolaou, P. Heretsch, A.E. Marrouni, C.R.H. Hale, K.K. Pulukuri, A.K. Kudva, V. Narayan, K.S. Prabhu— 2014

A catalytic asymmetric total synthesis of the potent and selective antileukemic Δ12-prostaglandin J3 (Δ12-PGJ3) 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.

Title18. Total Synthesis of Δ12-Prostaglandin J3, a Highly Potent and Selective Antileukemic Agent
AuthorK.C. Nicolaou, P. Heretsch, A.E. Marrouni, C.R.H. Hale, K.K. Pulukuri, A.K. Kudva, V. Narayan, K.S. Prabhu
Date2014
IdentifierDOI: 10.1002/anie.201404917
Source(s)
CitationAngew. Chem. Int. Ed. 2014, 53 10443-10447; Angew. Chem. 2014, 126 10611-10615