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An Ugi Reaction in the Total Synthesis of (−)-Dysibetaine

✍ Scribed by Jerry Isaacson; Yoshihisa Kobayashi

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
295 KB
Volume
48
Category
Article
ISSN
0044-8249

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✦ Synopsis

Abstract

(−)‐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.magnified image

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