A concise synthetic method towards (-)-swainsonine and its 8-epimer by using palladium-catalyzed asymmetric hydroamination of alkoxyallene as the key strategy

作者：Lim Wontaeck; Rhee Young Ho^*

来源：Tetrahedron, 2015, 71(35): 5939-5945.

DOI：10.1016/j.tet.2015.05.034

• Pi-allyl complex
• Hydroamination
• Asymmetric synthesis
• (-)-Swainsonine
• N,O-Acetal

A concise and flexible formal synthesis of (-)-swainsonine and the 8-epimer is reported. The synthesis features sequential Pd-catalyzed asymmetric hydroamination of alkoxyallene and the Ru-catalyzed ring-closing-metathesis as the key strategy, which generates cyclic allylic N,O-acetal as the pivotal intermediate. Notably, this reaction could be performed on a multigram-scale. In addition, both the natural product and its 8-epimer could be obtained with comparable synthetic efficiency.

• 出版日期2015-9-2