Intramolecular imino Diels-Alder reaction: progress toward the synthesis of uncialamycin.
We herein described an intramolecular imino Diels-Alder reaction promoted with BF(3).OEt(2)/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product.
Desrat
Sandy
S
EA Substances Lichéniques et Photoprotection, Faculté des Sciences Biologiques et Pharmaceutiques, Université de Rennes 1, France.
van de Weghe
Pierre
P
D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002625:Chemistry, Organic / Q000379:methods*; D002626:Chemistry, Pharmaceutical / Q000379:methods; D008956:Models, Chemical; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry; D013237:Stereoisomerism; D014961:X-Ray Diffraction
D000475:Alkenes; D000480:Alkynes; D000880:Anthraquinones; D000890:Anti-Infective Agents; D011804:Quinolines; C512009:uncialamycin; D010100:Oxygen