Banfi Luca, Basso Andrea, Guanti Giuseppe, Riva Renata
Università degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, 16146 Genova, Italy.
Mol Divers. 2003;6(3-4):227-35. doi: 10.1023/b:modi.0000006778.42751.7f.
beta-Acylamino-alpha-hydroxyamides and beta-acylamino-alpha-oxoamides, compounds known to be potent protease inhibitors, can be conveniently prepared with a highly convergent strategy involving a Passerini multicomponent reaction between a N-protected alpha-aminoaldehyde, a carboxylic acid and an isocyanide. After N-deprotection and concomitant acyl migration the desired beta-acylamino-alpha-hydroxyamide moiety is obtained and can be further elaborated, for example via oxidation of the secondary alcohol group. In this paper we report the studies that have been carried out in order to transfer this synthetic methodology onto polystyrene resin, using a photocleavable linker and a N-Boc protecting strategy.
β-酰氨基-α-羟基酰胺和β-酰氨基-α-氧代酰胺是已知的强效蛋白酶抑制剂，可通过一种高度汇聚的策略方便地制备，该策略涉及N-保护的α-氨基醛、羧酸和异氰化物之间的Passerini多组分反应。在N-脱保护并伴随酰基迁移后，可得到所需的β-酰氨基-α-羟基酰胺部分，并且可以进一步进行修饰，例如通过仲醇基团的氧化。在本文中，我们报告了为了将这种合成方法转移到聚苯乙烯树脂上而进行的研究，使用了光可裂解连接子和N-Boc保护策略。
