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

TETRAHEDRON

卷:73

Article

Zhang, Yun²  Xue, Yibin¹  Luo, Tuoping¹ 

[1] Peking Univ, Acad Adv Interdisciplinary Studies, Key Lab Bioorgan Chem & Mol Engn,Minist Educ, BNLMS,Coll Chem & Mol Engn,PekingTsinghua Ctr Lif, Beijing 100871, Peoples R China

[2] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

关键词: Total synthesis;    Indole alkaloids;    Mersicarpine;    Cycloaddition;    Rearrangement;   

DOI  :  10.1016/j.tet.2016.11.049

来源: Elsevier

【 摘 要 】

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. (C) 2016 Elsevier Ltd. All rights reserved.

【 授权许可】

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