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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 12
131
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Original Articles

New Synthetic Route to Pummerer's Ketone

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Pages 1783-1792 | Accepted 20 Feb 1992, Published online: 23 Sep 2006
 

Abstract

Pummerer's ketone 1 is obtained with an overall yield of 55 % by the following sequence: Claisen rearrangement of an arylcyclohexylether 3; allylic oxidation of the methylcycloalkylphenolic derivative 4b, then spontaneous cyclisation during demethylation to give 2. 1 is obtained by dehydrogenation of 2. NMR data agree with a cis stereochemistry at C4a and C 9b.

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