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Synlett 1990; 1990(4): 233-234
DOI: 10.1055/s-1990-21048
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The Pechmann Reaction and Regioselective Oxidation with Selenium Dioxide. Synthesis of the 12-Demethoxydefucogilvocarcin Ring System

Duy H. Hua* , Shankar Saha, Jin Coo Maeng, Didier Bensoussan
  • *Department of Chemistry, Kansas State University, Manhattan, Kansas 66506, USA
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Publication Date:
08 March 2002 (online)

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The Pechmann condensation of resorcinol with ethyl 2-oxocyclohexanecarboxylate and ethyl (2-oxocyclohexyl)acetate provided pyrone 3 (3-hydroxy-6-oxo-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran) and seven-membered lactone 5 (3-hydroxy-6-oxo-6,7,8,9,10,11-hexahydrodibenz[b,d]oxepin), respectively. Condensation of 1,5-dihydroxynaphthalene with ethyl 2-oxocyclohexanecarboxylate followed by regioselective oxidation with selenium dioxide and dehydrogenation with Pd/C furnished the 12-demethoxydefucogilvocarcin ring system 12 (1,10-dimethoxy-6-oxo-6H-benzo[d]naphtho[1,2-b]pyran) in five steps and 38% over-all yield.

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