Synlett 2009(2): 292-296  
DOI: 10.1055/s-0028-1087521
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclohepta[de]naphthalenes and the Rearranged Abietane Framework of Microstegiol via Nicholas Reaction Chemistry

Rafiq A. Taj, Anusha Abhayawardhana, James R. Green*
Department of Chemistry and Biochemistry, University of Windsor, Windsor, ON, N9B 3P4, Canada
Fax: +1(519)9737098; e-Mail: jgreen@uwindsor.ca;
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Publikationsverlauf

Received 30 September 2008
Publikationsdatum:
15. Januar 2009 (online)

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Abstract

Nicholas reactions on 2,7-dioxygenated naphthalenes give C-1 monosubstitution and C-1/C-8 disubstitution in most ­cases. From γ-carbonyl cation monocondensation product 3b or alkyne-unsubstituted dicondensation product 4a, cyclohepta[de]naphthalenes bearing no substituents, gem-dimethyl substituents, and a ketone function, and the rearranged abietane framework of microstegiol may be prepared.

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