Hyphenating the curtius rearrangement with Morita-Baylis-Hillman adducts: synthesis of biologically active acyloins and vicinal aminoalcohols

Journal of the Brazilian Chemical Society

W. Amarante, Giovanni¹  Coelho, Fernando¹  Universidade de Campinas, Campinas, Brazil¹  Cavallaro, Mayra¹ 

关键词: Curtius rearrangement;    Morita-Baylis-Hillman;    drugs;    aminoalcohols;    acyloins;   

DOI  :  10.1590/S0103-50532011000800022

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

Using Morita-Baylis-Hillman adducts as substrates, the Curtius rearrangement was performed in a sequence that allowed the synthesis of several hydroxy-ketones (acyloins) with great structural diversity and in good overall yields. These acyloins in turn were easily transformed into 1,2-anti aminoalcohols through a highly diastereoselective reductive amination step. The synthetic utility of these approaches was exemplified by performing the syntheses of (±)-bupropion, a drug used to treat the abstinence syndrome of smoker and (±)-spisulosine, a potent anti-tumoral compound originally isolated from a marine source.

【 授权许可】

Unknown