Asymmetric Synthesis of 1-Aza-4-deoxypicropodophyllotoxin

作者：Aigret Benoit M; Jacobs Jeroen; Van Meervelt Luc; De Borggraeve Wim M^*

来源：Synlett, 2013, 24(9): 1097-1100.

DOI：10.1055/s-0033-1338414

• Mannich bases
• asymmetric catalysis
• amino aldehydes
• enantioselectivity
• total synthesis

In our search for new easily accessible analogues based on the natural product podophyllotoxin, we synthesized 1-aza-4-deoxypicropodophyllotoxin in good overall yield and excellent enantioselectivity. The synthesis was centered around a direct asymmetric Mannich reaction using D-proline as the key step for introduction of the chiral centres. Our synthesis of 1-aza-4-deoxypodophyllotoxin was hindered through the increased instability towards epimerization of the C2 position. We did, however, synthesized a new scaffold based on the opened lactone analogue.

• 出版日期2013-6