C ARYLGLYCOSIDES VIA BENZANNULATION MEDIATED BY FISCHER CHROMIUM CARBENE COMPLEX

不饱和Fischer铬的[3+2+1]环加成反应 卡宾络合物和炔烃(Dvtz反应)提供两种 C-芳基糖苷合成的补充方法。小说 合成了糖基化的Fischer铬卡宾配合物7和8 通过卡宾阴离子与C-1甲酰基之间的Aldol反应 碳水化合物衍生物。配合物7和8进行环加成反应 与TMS-乙炔一起提供C-芳基糖苷衍生物9和10。 烯基卡宾铬配合物11的第二种环加成反应 C-炔基糖苷12-16提供C-芳基糖苷19-23。在这两个地方 糖基化芳环的区域化学探讨 由公认的Dvtz反应机制建立，并 建立酚羟基与碳水化合物的邻位。 这种区域化学是Natural的一个共同的结构特征 发生C-芳基糖苷。

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.