Weiss-Cook Condensations

Synthesis of c/s-bicyclo[3.3.0]octane-3,7-dione. The product is frequently decar-boxylated. 

Name Reactions A Collection of Detailed Mechanisms and Synthetic Applications, DOI 10.1007/978-3-319-03979-4 284, Springer International Publishing Switzerland 2014 

Edwards, J. M. Tetrahedron Lett. 1968, 9, 4885 887. Weiss was a scientist at the National Institutte of Health in Bethesda, Maryland. 

Gawish, A. Weiss, U. Orga. Synth. 1986, 64, 27-38. James M. Cook is a professor at University of Wiseonsin, Milwaukee. 

Galatsis, P. Weiss-Cook Reaction, In Name Reactions for Carbocyclic Ring Formations, Li, J. J., Ed. Wiley Hoboken, NJ, 2010, pp 181-196. (Review). 

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The approach to 731 developed by Dauben and Walker, outlined in Scheme LXXXII, begins with the Weiss-Cook condensation of 743 and proceeds after hydrolysis and monoketalization to furnish keto acid 744. Wolff-Kishner reduction, cycliza-tion, and methylation of this intermediate provided diketone 745 which was transformed by standard means to 746, a molecule which had previously been carried on to 731 (Scheme LXXX). 

Wei Y, Mizzen CA, Cook RG, Gorovsky MA, Allis CD (1998) Phosphorylation of histone H3 at serine 10 is correlated with chromosome condensation during mitosis and meiosis in Tetrahymena. Proc Natl Acad Sci U S A 95 7480-7484... 

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