Convenient Syntheses of 5, 5, 9-Trimethyl-trans-1-decalone and 6β-Hydroxy-5, 5, 9β-trimethyl-trans-1-decalone

David L. Snitman, Mei Yuan Tsai, David S. Watt, Charles L. Edwards, Philip L. Stotter

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44 Scopus citations


Convenient syntheses of 5, 5, 9-trimethyl-trarcs-1-decalone (1) and 6β-hydroxy-5, 5, 9β-trimethyl-frans-1-decalone (2) involve (1) the Robinson annelation of 2-methyl-1, 3-cyclohexanedione with ethyl vinyl ketone, (2) selective ketalization of 5, 9-dimethyl-Δ5, 10-octal-1, 6-dione at the nonconjugated carbonyl group with ethylene glycol, (3) reductive methylation of 1-ethylenedioxy-5, 9-dimethyl-Δ5, 10-2-octalone, (4) Wolff-Kishner reduction or dissolving-metal reduction of 1-ethylenedioxy-5, 5, 9-trimethyl-trans-1-decalone, and (5) acid-catalyzed hydrolysis of 1-ethylenedioxy-5, 5, 9-trimethyl-trans, 9β-trimethyl-trans-decalin to form 1 and 2, respectively.

Original languageEnglish
Pages (from-to)2838-2842
Number of pages5
JournalJournal of Organic Chemistry
Issue number16
StatePublished - Feb 1 1979

ASJC Scopus subject areas

  • Organic Chemistry


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