Synthesis of dihydrooxepin models related to the antitumor antibiotic MPC1001.
4-Hydroxy-L-proline was converted into the tetrahydrooxepino[4,3-b]pyrrole ring system characteristic of the potent antitumor agent MPC1001. Key steps were regioselective formation of a vinylogous amide by use of Bredereck's reagent and acid-induced cyclization of an alcohol onto the carbon-carbon double bond of that amide by addition-elimination to generate the seven-membered oxacyclic subunit.
Peng
Jianbiao
J
Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Clive
Derrick L J
DL
D000903:Antibiotics, Antineoplastic / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D010082:Oxepins / Q000138:chemical synthesis* / Q000494:pharmacology
D000903:Antibiotics, Antineoplastic; D006576:Heterocyclic Compounds, 4 or More Rings; C493112:MPC1001; D010082:Oxepins