Synlett 2009(15): 2445-2448  
DOI: 10.1055/s-0029-1217738
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of trans-Fused Sesquiterpenoid Analogues by Zirconocene-Mediated Metallo-ene Reaction

Aleš Korotvičkaa, Simona Hybelbauerováb,c, Martin Kotora*a,c
a Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech ­Republic
Fax: +420(221)951324; e-Mail: kotora@natur.cuni.cz;
b Department of Teaching and Didactics of Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic
c Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo N. 2, 166 10 Praha 6, Czech Republic
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Publication History

Received 30 June 2009
Publication Date:
27 August 2009 (online)

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Abstract

Dibutyl zirconocene-mediated trans-selective cyclization of methoxyallyl-ene followed by the reaction with electrophiles is a convenient method for the synthesis of functionalized cyclopentane derivatives. Ring-closing metathesis of the obtained cyclopentane derivative yielded a common building block for the synthesis of sesquiterpene analogues with unnatural trans-[3.4.0]bicyclo-nonane skeleton.

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For discussion of the formation of the more thermo-dymically stable trans-substituted zirconacyclopentane intermediate, see ref. 7.