Intramolecular Photocycloaddition of N-Alkenyl Substituted Maleimides: A Potential Tool for the Rapid Construction of Perhydroazaazulene Alkaloids

Kevin I. Booker-Milburn*, Christopher E. Anson, Cole Clissold, Nicola J. Costin, Richard F. Dainty, Martin Murray, Dhiren Patel, Andrew Sharpe

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

39 Citations (Scopus)

Abstract

UV irradiation of a number of N-alkenyl-substituted maleimide derivatives leads to the formation of complex perhydroazaazulenes in excellent yields. The overall process can be considered as a formal intramolecular [5+2] cycloaddition. Substrates were prepared by Mitsunobu coupling of the appropriate alkenols with various maleimides. Methyl substitution of the alkenyl side chain gave the cycloadducts 13ag in good yields, with moderate to high stereoselectivity being observed for 13e and 13g, respectively. Use of cyclic alkene side chains led to the formation of tri- and tetracyclic products with high degrees of stereoselectivity in most cases. Some of the polycyclic ring systems that were prepared constitute the core skeleton of a number of complex alkaloids. The substrate 29 underwent an unexpected [2+2] photocycloaddition to yield the unusual cyclobutane 31.
Translated title of the contributionIntramolecular Photocycloaddition of N-Alkenyl Substituted Maleimides: A Potential Tool for the Rapid Construction of Perhydroazaazulene Alkaloids
Original languageEnglish
Pages (from-to)1473-1482
Number of pages10
JournalEuropean Journal of Organic Chemistry
Volume2001
Issue number8
Early online date9 Mar 2001
DOIs
Publication statusPublished - 28 Apr 2001

Keywords

  • Alkaloids
  • Cycloadditions
  • Maleimides
  • Nitrogen heterocycles
  • Photochemistry

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