C ARYLGLYCOSIDES VIA BENZANNULATION MEDIATED BY FISCHER CHROMIUM CARBENE COMPLEX

通过 Fischer 铬卡宾络合物介导的苯环化反应生成 C 芳基糖苷

• 批准号: 6118579
• 负责人: SHON R PULLEY
• 金额: $ 0.06万
• 依托单位: WASHINGTON UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1998
• 资助国家: 美国
• 起止时间: 1998-08-01 至 1999-07-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6118579
• 关键词: biological products; biomedical resource; spectrometry

A [3+2+1] cycloaddition between unsaturated Fischer chromium carbene complexes and alkynes (the Dvtz reaction) provides two complementary approaches to the synthesis of C-arylglycosides. Novel glycosylated Fischer chromium carbene complexes 7 and 8 were prepared via an aldol reaction between carbene anions and C-1 formyl carbohydrate derivatives. Complexes 7 and 8 undergo cycloaddition with TMS-acetylene to provide C-arylglycoside derivative 9 and 10. In a second approach cycloaddition of alkenyl chromium carbene complex 11 and C-alkynylglycosides 12-16 affords C-arylglycosides 19-23. In both approaches the regiochemistry of the glycosylated aromatic ring is established by the accepted mechanism for the Dvtz reaction and establishes the phenolic hydroxyl group ortho to the carbohydrate. This regiochemistry is a common structural feature of naturally occurring C-arylglycosides.

不饱和菲舍尔铬间的[3+2+1]环加成