Isaacson Jerry, Kobayashi Yoshihisa
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive Mail Code 0343, La Jolla, CA 92093-0343, USA.
Angew Chem Int Ed Engl. 2009;48(10):1845-8. doi: 10.1002/anie.200805709.
(-)-Dysibetaine has been synthesized in 11 steps from readily available L-malic acid (see scheme). The key step is a unique Ugi 4-center-3-component cyclization reaction, where an ester group acts as the carboxylic acid component. The use of 1,1,1,3,3,3-hexamethyldisilazane as an ammonia equivalent and a specially designed isocyanide leads to an expeditious synthesis.