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Merck

An Ugi reaction in the total synthesis of (-)-dysibetaine.

Angewandte Chemie (International ed. in English) (2009-01-29)
Jerry Isaacson, Yoshihisa Kobayashi
RESUMEN

(-)-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.

MATERIALES
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