[Studies on the spirocompounds: synthesis of 10-methyl spiro [4.5]dec-6-en-6-carboxylic acid].
3-Methyl-cyclohexenone 4 spiroannulates with 1, 4-dibromobutane in NaNH2/NH3 or t-BuOK/benzene to afford not only the main monospiro compounds 5a and 5b but also the dispiro compounds 6a and 6b. The title compound 11 was synthesized from 5 through the following steps: Catalytic hydrogenation of the spiro olefinic compounds, addition of trimethylsilycyanide to the carbonyl group, hydrolysis of the siloxyl ether, dehydration of the cyanohydrin and hydrolysis of the cyano group.
Zheng
W J
WJ
Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing.
Chen
S F
SF
D000777:Anesthetics; D000818:Animals; D006993:Hypnotics and Sedatives; D051379:Mice; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013141:Spiro Compounds
D000777:Anesthetics; D006993:Hypnotics and Sedatives; D012717:Sesquiterpenes; D013141:Spiro Compounds; C067945:10-methyl spiro(4.5)dec-6-en-6-carboxylic acid