Wender synthesis

There are numerous other syntheses of indoles, and a modern example is the Wender synthesis. Here a 2-bromo-iV-(trifluoroacetyl)aniline in THF is deprotonated by butyllithium and then, in the same pot, reacted with fert-butyllithium to effect halogen-metal exchange to give the dilithiated derivative. To this intermediate is added an a-bromo ketone. A carbon-carbon bond is established first between the reactants, and then cyclization occurs to form a hydroxyindoline. Finally, dehydration generates the indole (Scheme 7.16). 

The Wender synthesis was reported in two communcations in 1997 435, 436), but the full papers have yet to appear. The synthesis is linear of the form A- AB- ABC- ABCD, but it is very different from the formally similar Holton approach. 

E. Caldera22o, R. Ercoh, and G. Natta, iu I. Wender and P. Piuo, eds.. Organic Synthesis via Metal Carbonyls, Wiley-Interscience, New York, 1968,... 

Wender and Aube have independently described the use of the Bischler-Napieralski reaction in the synthesis of Yohimban alkaloids. Aube s approach involved the cyclization of indole 50 followed by reduction of the resulting dihydroisoquinoline... 

Wender P. A., Love J. A. The Synthesis of Seven-Memhered Rings General Strategies and the Design and Development of a New Class of Cycloaddition Reactions Adv. Cydoaddit. 1999 5 1-45... 

Wender, P.A., Mitchell, D.J., Pelkey, E.T., Steinman, L., and Rothbard, J.B. Xhe design, synthesis, and evaluation of molecules that enable or enhance cellular uptake Peptoid molecular transporters. Proc. Nad. Acad. Sci. USA 2000, 97, 13003-13008. 

Wender, P. Miller, B.L. (1993) Toward the Ideal Synthesis Connectivity Analysis and Multibond-Forming Processes. In Organic Synthesis Theory and Applications, Vol. 2 (ed. T. Hudlicky), pp. 27-65. JAl Press, Greenwich, CT. 

Wender, P.A., Schaus, J.M., White, A.M. (1980) General Methodology for cis-Hydroisoquinoline Synthesis Synthesis of Reserpine. Journal of the American Chemical Society, 102, 6157-6159. 

Wender, P.A. (1996) Frontiers in Organic Synthesis Introduction. Chemical Reviews, 96, 1-2. 

The synthesis of the Taxol in Scheme 13.56 by P. A. Wender and co-workers at Stanford University began with an oxidation product of the readily available terpene pinene. One of the key early steps was the photochemical rearrangement in Step B. 

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