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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.

Title
Total Synthesis of Δ12-Prostaglandin J3, a Highly Potent and Selective Antileukemic Agent
Author
K.C. Nicolaou, P. Heretsch, A.E. Marrouni, C.R.H. Hale, K.K. Pulukuri, A.K. Kudva, V. Narayan, K.S. Prabhu
Date
2014
Identifier
DOI: 10.1002/anie.201404917
Citation
Angew. Chem. Int. Ed. 2014, 53 10443-10447; Angew. Chem. 2014, 126 10611-10615