An approach to the synthesis of neplanocin A

…, CA Booth, BM Foxman, BB Snider

文献索引：Faith; Booth; Foxman; Snider Journal of Organic Chemistry, 1985 , vol. 50, # 11 p. 1983 - 1985

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被引用次数: 23

摘要

Treatment of 3 with bromine in CH2C12 gave 5 in 75% yield. Nitrogen participation in the rearrangement is well precedented in similar systems. 6 All attempts to convert 5 to 7 were unsuccessful. For increased solubility and prevention of participation of the amide anion, lactam 3 was benzylated with KOH and benzyl bromide in Me2S0 and gave 4 in 71% yield. Bromination of 4 as above gave 6 in quantitative yield. In contrast to 5, 6 underwent facile ...