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

Aleš Korotvička; Simona Hybelbauerová; Martin Kotora

doi:10.1055/s-0029-1217738

LETTER

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

Aleš Korotvička^a, Simona Hybelbauerová^b,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

Abstract

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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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References

References and Notes

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