We herein described an intramolecular imino Diels-Alder reaction promoted with BF3.OEt2/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quitioline moiety of the uncialamycin, a new enediyne natural product

Desrat, S

van de Weghe, P

English

International audienceWe herein described an intramolecular imino Diels−Alder reaction promoted with BF3·OEt2/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product

Desrat, Sandy

van de Weghe, Pierre

HAL: Hyper Article en Ligne

Intramolecular Imino Diels−Alder Reaction: Progress toward the Synthesis of Uncialamycin

Portail HAL UNIV-RENNES

Sandy  Desrat

Pierre van de Weghe

Crossref

Van De Weghe, Pierre

Archive Ouverte en Sciences de l'Information et de la Communication

UCL Discovery

(b) For a review concerning the imino Diels-Alder reaction, see:

Although the imine 10 was quantitatively obtained after treatment of the reaction mixture, the yield after isolation is low because a part of the imine was decomposed during the silica gel column chromatography.

and references cited therein. (b) Vander Mierde, H.;

Chiralpack AD-H column (5 mm, 4.6x250 mm) with a UV detection at 259 nm at 20 °C,

Examples of [4+2] cycloaddition affording quinoline derivatives, see: (a) Alvès,

Intramolecular Imino Diels-Alder Reaction: Progress toward the Synthesis of Uncialamycin

Intramolecular Imino Diels-Alder Reaction: Progress toward the Synthesis of Uncialamycin

Abstract

Similar works

Full text

Available Versions

HAL: Hyper Article en Ligne

Portail HAL UNIV-RENNES

Crossref

Archive Ouverte en Sciences de l'Information et de la Communication

UCL Discovery