作者:Narihiko Fukamiya、Michiharu Kato、Akira Yoshikoshi
DOI:10.1039/p19730001843
日期:——
The total synthesis of (±)-seychellene (4,7,8-trimethyl-11-methylenetricyclo[5.3.1.03,8]undecane)(I) from2,3-di-methylcyclohex-2-en-1-one (XIV) is described. The ketone (XIV) was converted into 2-methyl-2-(3-methyl-5-iodopentyl)-3-methylenecyclohexan-1-one (XV), which gave 2-methyl-2-(3-methyl-5-iodopentyl)-3-bromo-methylcyclohexa-3,5-dien-1-one (XIX) with N-bromosuccinimide. Treatment of bromo-ketone
由(2,3-di-methylcyclohex-2-en-1-one(())合成(±)-seychellene(4,7,8-三甲基-11-亚甲基三环[5.3.1.0 3,8 ]十一烷)(I)( XIV)被描述。将酮(XIV)转化为2-甲基-2-(3-甲基-5-碘戊基)-3-亚甲基环己-1--1-酮(XV),得到2-甲基-2-(3-甲基-5-碘代戊基)-3-溴代甲基环己-3,5-二烯-1-酮(XIX)与N-溴代琥珀酰亚胺。用氯化铬(II),然后用酸处理溴代酮(XIX),得到2,3-二甲基-2-(3-甲基-5-碘戊基)环己-3,5-二烯-1-酮(XXI)。从二烯酮(XXI)获得2,3-二甲基-2-(3-甲基-5-二甲基氨基戊基)环己基3,5-二烯-1-酮(XXII)并被氧化;裂解生成的N-氧化物,生成4,7,8-三甲基三环-[5.3.1.0 3,8] undec-9-en-11-one(VII