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

Authors

Rafiq A. Taj
Anusha Abhayawardhana
James R. Green, University of WindsorFollow

Document Type

Article

Publication Date

2009

Publication Title

Synlett

Issue

2

First Page

292

Keywords

carbocations, alkyne complexes, transition metals, electrophilic aromatic substitution, ring closure, tautomerism

Last Page

296

Abstract

Nicholas reactions on 2,7-dioxygenated naphthalenes give C-1 monosubstitution and C-1/C-8 disubstitution in most cases. From gamma-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.

DOI

10.1055/s-0028-1087521

Comments

The article available for download is the Accepted Version. The definitive version is published in Synlett and is available here. Copyright (2012) Georg Thieme Verlag KG.

Recommended Citation

Taj, Rafiq A.; Abhayawardhana, Anusha; and Green, James R.. (2009). Cyclohepta[de]naphthalenes and the Rearranged Abietane Framework of Microstegiol via Nicholas Reaction Chemistry. Synlett (2), 292-296.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/11