The Development of a Convergent and Efficient Enantioselective Synthesis of the Bengamides via a Common Polyol Intermediate
作者:Robert K. Boeckman, Jr.、Tammy J. Clark、Brian C. Shook
DOI:10.1002/hlca.200290026
日期:2002.12
the bengamide family of antitumor agents from a common polyol thioester is described. Consecutive aldol condensations afford the protected polyol thioester side chain suitable for coupling to the bengamides. A novel chiral-phase-transfer-catalyzed enantioselective alkylation affords the properly functionalized caprolactams required for the synthesis of more-complex members of the bengamide family. Use
描述了一种从普通的多元醇硫酯到抗肿瘤剂苯甲酰胺家族的有效,通用的合成途径。连续的醛醇缩合得到适合于偶联至苯甲酰胺的被保护的多元醇硫酯侧链。一种新颖的手性相转移催化的对映选择性烷基化提供了合成苯甲酰胺家族中更复杂成员所需的适当官能化的己内酰胺。与对映选择性的羟醛缩合所需的硼路易斯酸相容的甲基2-萘基醚保护基的使用,可直接获得所有的苯甲酰胺。