- A new synthesis of flindersine
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Ketene S,N-acetal from the carbethoxylated isobutyl methyl ketone undergoes thermal cyclization with N-phenyl to give 4-hydroxy-3-(3-methylbutanoyl)-2-thiomethylquinoline (III) which is transformed into the corresponding 4-chloro derivative (IV).The carbonyl group in the side chain at 3-position of VI is converted into the α,β-unsaturated ketone (V) followed by acid hydrolysis to afford 4-keto-2,2-dimethyl-3,4,5,6-tetrahydro-2H-pyranoquinolin-5-one (VI).Reduction of 4-keto group of VI and subsequent dehydration of the resulting alcohol furnishes flindersine (I).
- Anand, R C,Sinha, A K
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p. 560 - 562
(2007/10/02)
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