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Synlett 2009(15): 2445-2448
DOI: 10.1055/s-0029-1217738
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
Further Information
Received
30 June 2009
Publication Date:
27 August 2009 (online)
Publication History
Publication Date:
27 August 2009 (online)
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 and Notes
For discussion of the formation of the more thermo-dymically stable trans-substituted zirconacyclopentane intermediate, see ref. 7.