Diels-Alder reaction of α-tropolone and electron-deficient dienophiles prompted by Et3N or silica gel: a new synthetic method of highly functionalized homobarrelenone derivatives

Hiroaki Okamura, Hiroki Iiji, Toshiyuki Hamada, Tetsuo Iwagawa, Hiroshi Furuno

    Research output: Contribution to journalArticlepeer-review

    13 Citations (Scopus)

    Abstract

    A Diels-Alder reaction of α-tropolone and electron-deficient dienophiles prompted by Et3N or silica gel was performed. Reaction with the highly reactive dienophile, N-methylmaleimide, proceeded smoothly in the presence of Et3N or silica gel to yield adducts as a mixture of endo and exo isomers. Both catalysts accelerated endo/exo isomerization of the product, and detailed examination of the reaction using hinokitiol and N-methylmaleimide revealed that isomerization proceeds via an intramolecular path without retro Diels-Alder reaction. Successful cycloaddition reactions were established with six other dienophiles: acrylonitrile, methyl acrylate, ethyl vinyl ketone, dimethyl fumalate, dimethyl malate, and dimethyl acetylenedicarboxylate, and the corresponding adducts were obtained in good to moderate yields.

    Original languageEnglish
    Pages (from-to)10709-10714
    Number of pages6
    JournalTetrahedron
    Volume65
    Issue number51
    DOIs
    Publication statusPublished - Dec 19 2009

    All Science Journal Classification (ASJC) codes

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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