Asymmetric syntheses of 6-deoxyfagomin, D-deoxyrhamnojirimycin, and D-rhamnono-1,5-lactam

作者：Fu Rui; Du Yu; Li Zhao Ying; Xu Wei Xuan; Huang Pei Qiang^*

来源：Tetrahedron, 2009, 65(47): 9765-9771.

DOI：10.1016/j.tet.2009.09.083

• Aza-sugars
• Asymmetric synthesis
• Building block
• Samarium diiodide

N-Allyl protected 3-O-benzyloxglutarimide 11 was synthesized as a useful variant of the chiral building block 10. This modification allowed a high-yielding deprotection of the allyl group from the lactam intermediate 14. Starting from this building block, the asymmetric syntheses of aza-sugars 6-deoxyfagomine (2), D-rhamnono-1,5-lactam (6), as well as D-deoxyrhamnojirimycin (5) have been achieved in high regio- and/or diastereo-controlled manner.

• 出版日期2009-11-21
• 单位厦门大学