TY - JOUR
T1 - Convenient Syntheses of 5, 5, 9-Trimethyl-trans-1-decalone and 6β-Hydroxy-5, 5, 9β-trimethyl-trans-1-decalone
AU - Snitman, David L.
AU - Tsai, Mei Yuan
AU - Watt, David S.
AU - Edwards, Charles L.
AU - Stotter, Philip L.
PY - 1979/2/1
Y1 - 1979/2/1
N2 - 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.
AB - 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.
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U2 - 10.1021/jo01330a004
DO - 10.1021/jo01330a004
M3 - Article
AN - SCOPUS:0010402290
SN - 0022-3263
VL - 44
SP - 2838
EP - 2842
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 16
ER -