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Stereo-controlled synthesis of polyheterocycles via the diene-transmissive hetero-Diels-Alder reaction of ß,γ-unsaturated α-keto esters.
Otani, Takashi; Tamai, Yumiko; Seki, Kazunori; Kikuchi, Tomohiro; Miyazawa, Taiichiro; Saito, Takao.
Affiliation
  • Otani T; Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan. tsaito@rs.kagu.tus.ac.jp.
Org Biomol Chem ; 13(21): 5875-9, 2015 Jun 07.
Article in En | MEDLINE | ID: mdl-25920697
ABSTRACT
We describe the stereoselective synthesis of polyring-fused heterocyclic compounds based on diene-transmissive hetero-Diels-Alder reactions utilizing ß,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.
Subject(s)

Full text: 1 Database: MEDLINE Main subject: Polyenes / Cycloaddition Reaction / Heterocyclic Compounds Language: En Year: 2015 Type: Article

Full text: 1 Database: MEDLINE Main subject: Polyenes / Cycloaddition Reaction / Heterocyclic Compounds Language: En Year: 2015 Type: Article