An unexpected aziridination/rearrangement/oxidation tandem reaction leading to the total synthesis of (-)-mersicarpine

作者：Zhang, Yun; Xue, Yibin; Luo, Tuoping^*

来源：Tetrahedron, 2017, 73(29): 4201-4205.

DOI：10.1016/j.tet.2016.11.049

• Total synthesis
• Indole alkaloids
• Mersicarpine
• Cycloaddition
• Rearrangement

With the aim to synthesize anti-mitotic natural product (-)-rhazinal, we proposed a strategy based on a dearomative intramolecular [3+2] cycloaddition between alkyl azide and indole, followed by rearrangement to furnish the featured tetracyclic framework. During the reaction condition screening, we accidentally encountered a tandem [3+2] cycloaddition/rearrangement/oxidation reaction, which enabled the synthesis of another alkaloid, (-)-mersicarpine, in four steps with 35% overall yield from a reported intermediate. The tandem [3+2] cycloaddition/rearrangement reaction disclosed herein could provide a method for the synthesis of other structurally intriguing alkaloids.

• 出版日期2017-7-20
• 单位北京大学; 北京大学深圳研究生院