Development of Synthetic Methodologies for Heterocycles Using Diene-transmissive Hetero-Diels-Alder Reaction

  • Saito Takao
    Department of Chemistry, Faculty of Science, Tokyo University of Science
  • Kobayashi Satoru
    Central Pharmaceutical Research Institute, Japan Tabacco Inc.
  • Otani Takashi
    Course of Chemical Engineering, National Institute of Technology, Anan College
  • Kutsumura Noriki
    International Institute for Integrative Sleep Medicine (WPI-IIIS), University of Tsukuba

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Other Title
  • ジエン伝達ヘテロDiels-Alder反応を利用した複素環合成法の開発
  • ジエン デンタツ ヘテロ Diels-Alder ハンノウ オ リヨウ シタ フクソカン ゴウセイホウ ノ カイハツ

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<p>The diene-transmissive hetero-Diels-Alder reaction (DTHDA reaction) is a special case of the DTDA reaction in which one or more heteroatoms are contained within either a cross-conjugated triene/polyene (heterodendralene) π-system, a dienophile π-system or both. Therefore, the DTHDA protocol is an efficient and attractive method for the stereoselective synthesis of a variety of heterocyclic systems. Merits and potential of the DTHDA methodology for heterocyclic synthesis can be widely extended by structural variations and complexity of both diene and dienophile; the kind, numbers, and positions of heteroatoms contained in either the cross-conjugated triene/polyene ([3/n] heterodendralene) or the dienophile framework, as well as the inter- or intramolecular cycloaddition mode, and its predictable regio- and stereoselectivities. In this paper, we introduce the synthesis of a variety of heterocycles using the DTHDA reaction with a focus on our research.</p>

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