A concise and divergent approach to radicamine B and hyacinthacine A(3) based on a step-economic transformation

作者：Liao Jin Cheng; Xiao Kai Jiong; Zheng Xiao; Huang Pei Qiang^*

来源：Tetrahedron, 2012, 68(26): 5297-5302.

DOI：10.1016/j.tet.2012.01.085

• Step-economy
• Azasugars
• Alkaloids
• Glycosidase inhibitors
• Hantzsch ester

Based on our recently developed step-economic methodology of reductive alkylation of lactams/amides, we have developed a two-step synthesis of azasugar radicamine B (2a) and a four-step synthesis of azasugar hyacinthacine A(3) (5) from the common chiral building block 12. Hantzsch ester (HEH) was used as a milder hydride donor in the one-pot stereoselective reductive alkylation of lactam 12. The Wacker oxidation of fully substituted pyrrolidine derivative 2,5-trans-17 led to the synthesis of hyacinthacine A(3) (5). Compound 2,5-trans-17 could also serve as a plausible key intermediate for the synthesis of broussonetine sub-class of azasugars.

• 出版日期2012-7-1
• 单位厦门大学