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Synlett 1997; 1997(1): 25-26
DOI: 10.1055/s-1997-684
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Versatile Synthetic Approaches Towards Aza-analogues of Illudin and Ptaquilosin Sesquiterpenes

Beatrice Anichini, Andrea Goti, Alberto Brandi1 , Sergei I. Kozhushkov, Armin de Meijere2
  • 1Dipartimento di Chimica Organica “U. Schiff”, Centro di studio C. N. R. sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni, Università di Firenze, via G. Capponi 9, I-50121 Firenze, Italy, Fax 39 55 2476964; e-mail brandi@chimorg.unifi.it
  • 2Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany, Fax 49 551-399475; e-mail ameijer@gwdg.de
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Publication Date:
22 March 2004 (online)

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Indolizidinones with a α-spirocyclopropane group, obtained by 1,3-dipolar cycloaddition of chiral pyrroline nitrones to bicyclopropylidene, or methylenespiropentane, and thermal rearrangement of the adducts, have been synthesized as aza-analogous skeleton to the potent carcinogenic sesquiterpenes ptaquiloside and illudin. Their moderate DNA cleaving activity on a pUC18 DNA plasmid furnishes useful hints about structure-activity relationships for this class of compounds.

Illudin aza-analogues - 1,3-dipolar cycloaddition - chiral nitrones - bicyclopropylidene - methylenespiropentane

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