【摘要】 环戊二烯和乙醛酸经Diels-Alder环合、丁酰化、酶水解得(1R,4S,5R)-(–)-4-endo-4-羟基-2-氧杂二环[3.3.0]辛-7-烯-3-酮,再经LiAlH4还原、NaIO4氧化、NaBH4还原、乙酰化得(1R,2R)-2-乙酰氧基环戊-3-烯-1-甲醇乙酸酯,再经与2-氨基-6-环丙胺基-9H-嘌呤缩合、NaOH水解后制得抗艾滋病药物阿巴卡韦,总收率约3%(以乙醛酸计)。更多还原

【Abstract】 Cyclopentadiene and glyoxylic acid underwent the Diels-Alder reaction, acylation with butyric an-hydride, lipase enzymatic hydrolysis to get (1R,4S,5R)-(–)-4-endo-hydroxy-2-oxabicyclo[3.3.0]oct-7-en-3-one(4), which was successively reduced with LiAlH4, oxidized with NaIO4, reduced with NaBH4 and acelated with acetic anhy-dride to give (1R,2R)-2-acetoxycyclopent-3-en-1-methanol acetate(9). 9 was converted to an anti-HIV drug abacavir by condensation with 2-amino-6-cyclopropylamino-9H-purine and hydrolysis in sodium hydroxide solution.更多还原