Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA.
Org Lett. 2009 Mar 5;11(5):1143-6. doi: 10.1021/ol802992m.
Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived, masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.
通过采用β-内酰胺衍生的、掩蔽的双羟脯氨酸醛的Pictet-Spengler 反应，实现了葡糖苷酶抑制剂舒尔茨因 B 和 C 的对映选择性合成。随后的 Corey-Link 反应揭示了一个α-叠氮酸，使环化反应生成了与δ-内酰胺融合的四氢异喹啉。带有三硫酸盐侧链的有效合成方法包括 Noyori 氢化和 Sharpless 二羟基化。Corey-Link 过程中侧链上的仲胺的意外反应为脯氨酸和相关氨基酸衍生物的合成开辟了道路。
