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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
Further Information

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.

Key Words

zirconium - metallo-ene reaction - sesquiterpenoids - cyclization - metathesis

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