Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels-Alder reaction of β,γ-unsaturated α-keto esters.
We describe the stereoselective synthesis of polyring-fused heterocyclic compounds based on diene-transmissive hetero-Diels-Alder reactions utilizing β,γ-unsaturated α-keto esters. This protocol involves the initial endo- or exo-selective Diels-Alder (DA) reactions with electron-rich dienophiles, methylenation of the ester carbonyl groups with the Tebbe reagent, and a stereoselective second DA reaction with electron-deficient dienophiles. The use of enantioselective DA reactions in the initial reaction enables access to chiral polyring-fused heterocyclic compounds with multiple chiral centres.
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan. tsaito@rs.kagu.tus.ac.jp.
Takashi
T
Otani
Yumiko
Y
Tamai
Kazunori
K
Seki
Tomohiro
T
Kikuchi
Taiichiro
T
Miyazawa
Takao
T
Saito
D061565:Cycloaddition Reaction; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D004952:Esters; D006571:Heterocyclic Compounds; D007659:Ketones; D011090:Polyenes