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Synthesis 1996; 1996(4): 525-528
DOI: 10.1055/s-1996-4238
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Cascade Reactions of Methyl 2-Chloro-2-cyclopropylideneacetate with Five- and Seven-Membered Cyclic Dienolates: A Novel Approach to the Bicyclo[4.2.1]nonane Segment of the Skeleton of Mediterraneols

Lazaros Hadjiarapoglou, Iris Klein, Dietrich Spitzner1 , Armin de Meijere2
  • 1Institut für Chemie, Universität Hohenheim, Garbenstrasse 30, D-70599 Stuttgart, Germany, Fax +49(711)4592951; E-mail SPITZNER@RZ.UNI-HOHENHEIM.DE
  • 2Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany, Fax +49(551)399475; E-mail AMEIJER1@GWDG.DE
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Publication Date:
31 December 2000 (online)

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The MIMIRC (Michael-Michael-Ring Closure) reaction of methyl 2-chloro-2-cyclopropylideneacetate (5) with the cyclic dienolates 6a, 6c, and the one derived from 11-R under aportic conditions gave the tricyclic adducts 7a, 7c, and 10-R, respectively, in moderate to good yield. Compound 10-R is conceived as a potential intermediate for the synthesis of the biologically active marine diterpenes mediterraneol 1.

Michael reaction - aprotic - cascade reaction - tricyclo[4.2.1.02,8]nonanes - aldol reaction - retrograde - cyclopropanes - ”push-pull” substituted - bicyclo[4.2.1]nonanes

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