Literature DB >> 27172972

Total Synthesis of (+)-Minfiensine: Construction of the Tetracyclic Core Structure by an Asymmetric Cascade Cyclization.

Ze-Xin Zhang1, Si-Cong Chen1, Lei Jiao2.   

Abstract

A new method for one-step construction of the tetracyclic core structure of the indole alkaloid (+)-minfiensine was developed utilizing a palladium-catalyzed asymmetric indole dearomatization/iminium cyclization cascade. An efficient total synthesis of (+)-minfiensine was realized using this strategy. The present method enables access to the common core structure of a series of monoterpene indole alkaloids, such as vincorine, echitamine, and aspidosphylline A.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; cyclizations; natural products; palladium; total synthesis

Year:  2016        PMID: 27172972     DOI: 10.1002/anie.201602771

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

Authors:  Faben A Cruz; Yamin Zhu; Quentin D Tercenio; Zengming Shen; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

2.  Palladium Catalyzed Asymmetric Three-Component Coupling of Boronic Esters, Indoles, and Allylic Acetates.

Authors:  Santanu Panda; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2017-04-21       Impact factor: 15.419

3.  Efficient syntheses of (-)-crinine and (-)-aspidospermidine, and the formal synthesis of (-)-minfiensine by enantioselective intramolecular dearomative cyclization.

Authors:  Kang Du; He Yang; Pan Guo; Liang Feng; Guangqing Xu; Qinghai Zhou; Lung Wa Chung; Wenjun Tang
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825

Review 4.  The Chaotropic Effect as an Assembly Motif in Chemistry.

Authors:  Khaleel I Assaf; Werner M Nau
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-27       Impact factor: 15.336

5.  Modular Synthesis of Polycyclic Alkaloid Scaffolds via an Enantioselective Dearomative Cascade.

Authors:  James A Rossi-Ashton; Aimee K Clarke; Richard J K Taylor; William P Unsworth
Journal:  Org Lett       Date:  2020-01-15       Impact factor: 6.005

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.