An unexpected aziridination/rearrangement/oxidation tandem reaction leading to the total synthesis of (−)-mersicarpine. Issue 29 (20th July 2017)

• Record Type: Journal Article
• Authors: Zhang, Yun; Xue, Yibin; Luo, Tuoping
• Is Part Of: Tetrahedron. Volume 73:Issue 29(2017)
• Page Start: 4201
• Page End: 4205
• Publication Date: 2017-07-20
• Subjects: Total synthesis -- Indole alkaloids -- Mersicarpine -- Cycloaddition -- Rearrangement; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.11.049
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 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. Graphical abstract: