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A Ring Expansion−Annulation Strategy for the Synthesis of Substituted Azulenes. Preparation and Suzuki Coupling Reactions of 1-Azulenyl Triflates
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Department of Chemistry, Massachusetts Institute of Technology Cambridge, Massachusetts 02139
Org. Lett., 2001, 3 (7), pp 1081–1084
DOI: 10.1021/ol0156897
Publication Date (Web): March 14, 2001
Copyright © 2001 American Chemical Society
Section:Abstract
A new strategy for the synthesis of substituted azulenes is reported, based on the reaction of β‘-bromo-α-diazo ketones with rhodium carboxylates. The key transformation involves intramolecular addition of a rhodium carbenoid to an arene π-bond, electrocyclic ring opening, β-elimination, tautomerization, and trapping to produce 1-hydroxyazulene derivatives. The synthetic utility of the method is enhanced by the ability of the triflate derivatives to participate in Suzuki coupling reactions, as illustrated in a synthesis of the antiulcer drug egualen sodium (KT1-32).
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- Published In Issue April 05, 2001
- Received February 9, 2001
ACS
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