A domino N-amidoacylation/aldol-type condensation approach to the synthesis of the topo-I inhibitor Rosettacin and derivatives.
The pot, atom, and step-economic synthesis of Rosettacin topo-I poison and its derivatives has been achieved using a novel domino N-amidoacylation/aldol-type condensation, followed by decarboxylation of the ester function. The key domino procedure simply involves mixing HOBt ester as new reagent with lactam and NaH together in THF or THF/ DMF. The reaction seems to be general and led to suitable N-heterocyclic products in moderate to good yields.
Pin
Frédéric
F
URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex, France.
Comesse
Sébastien
S
Sanselme
Morgane
M
Daïch
Adam
A
D000215:Acylation; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D059004:Topoisomerase I Inhibitors
D004791:Enzyme Inhibitors; D006576:Heterocyclic Compounds, 4 or More Rings; D059004:Topoisomerase I Inhibitors; C528794:rosettacin