Sulphone-based elimination reactions in synthesis. Part 2. Diumycinol
作者:Philip Kocienski、Michael Todd
DOI:10.1039/p19830001783
日期:——
Diumycinol [2(Z), 6(E)-12-(2-methylene-6,6-dimethyl-1-cyclohexyl)-11-methylene-3,8,8-trimethyldodeca-2,6-dien-1-ol], a hydrolytic product of the antibiotic diumycin, was assembled from three fragments: 1-(2-phenylsulphonylethyl)-2-methylene-6,6-dimethylcyclohexane (28), 3-(2-iodoethyl)-3-methyloxetane (39), and (Z)-1-benzyloxy-6-phenylsulphonyl-3-methylhex-2-ene (3). An efficient synthesis of 2-methylene-6
地霉素[2(Z),6(E)-12-(2-亚甲基-6,6-二甲基-1-环己基)-11-亚甲基-3,8,8-三甲基十二烷基-2,6-二烯-1-抗生素yycin的水解产物ol]由三个片段组装而成:1-(2-苯基磺酰基乙基)-2-亚甲基-6,6-二甲基环己烷(28),3-(2-碘乙基)-3-甲基氧杂环丁烷( 39),和(Z)-1-苄氧基-6-苯基磺酰基-3-甲基己基-2-烯(3)。通过3,3-二甲基环己-1-烯基甲氧基甲基-锂的[2,3]σ重排可实现2-亚甲基-6,6-二甲基环己基甲醇(15)(γ-环香叶醇)的有效合成。