Asymmetric synthesis of (+)- and (−)-deoxyfebrifugine and deoxyhalofuginone

Zaidan, Raed K.; Smullen, Shaun; Evans, Paul

Asymmetric synthesis of (+)- and (−)-deoxyfebrifugine and deoxyhalofuginone

2015

Zaidan, Raed K. | Smullen, Shaun | Evans, Paul

Both enantiomers of deoxyfebrifugine (4) and deoxyhalofuginone (5), analogues of the quinazolinone-containing biologically active compounds febrifugine (1) and halofuginone (3), have been prepared in a six-step reaction sequence featuring an organocatalyzed Mannich reaction as the key stereo-inducing step. The compounds were isolated as their dihydrobromide salts in 29–42% overall yield and in 74–80% enantiomeric excess.

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