The catalytic asymmetric dearomatization of tryptamine for accessing meso-contiguous quaternary carbon centers of oligomeric cyclotryptamine alkaloids: a formal synthesis of hodgkinsine B-Reference-Cited by-同舟云学术

The catalytic asymmetric dearomatization of tryptamine for accessing meso-contiguous quaternary carbon centers of oligomeric cyclotryptamine alkaloids: a formal synthesis of hodgkinsine B

Published:2021 Issue:13 Volume:8 Page:3255-3259
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Wei Hongbo¹²³⁴⁵^ORCID,Chen Guzhou¹²³⁴⁵,Zou Huanhuan¹²³⁴⁵,Zhou Zhiqiang¹²³⁴⁵,Lei Pan¹²³⁴⁵,Yan Jiahang¹²³⁴⁵,Xie Weiqing¹²³⁴⁵^ORCID

Affiliation:

1. Shaanxi Key Laboratory of Natural Products & Chemical Biology

2. College of Chemistry & Pharmacy

3. Northwest A&F University

4. Yangling 712100

5. China

Abstract

Herein, we disclosed a catalytic asymmetric dearomatization (CADA) of tryptamine via tandem [4 + 2] cycloaddition/cyclization with o-azaxylylene in situ generated from functionalized 3-bromooxindole promoted by chiral N,N′-dioxide/Ni(BF₄)₂.

Funder

National Natural Science Foundation of China

Chinese Universities Scientific Fund

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/QO/D1QO00393C

Reference41 articles.

1. G. A. Cordell and J. E.Saxton , The Alkaloids: Chemistry and Physiology , ed. R. H. F. Manske and R. G. A. Rodrigo , Academic Press , New York , 1981 , vol. 20 , pp. 10–25

2. T. Hino and M.Nakagawa , The Alkaloids: Chemistry and Pharmacology , ed. A. Brossi , Academic Press , New York , 1989 , vol. 34 , pp. 1–75

3. U. Anthoni , C.Christophersen and P. H.Nielsen , in Alkaloids: Chemical and Biological Perspectives , ed. S. W. Pelletier , Permagnon , New York , 1999 , vol. 13 , pp. 163–236

4. Chimonanthine. A One-Step Synthesis and Biosynthetic Model

Cited by 11 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Visible-Light-Induced Dearomative Annulation of Indoles toward Stereoselective Formation of Fused- and Spiro Indolines;ACS Omega;2024-08-13

2. α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source;ChemistryOpen;2024-07-11

3. Lewis acid catalyzed stereospecific hydroxylation of chiral tertiary alkyl halides;Chemistry Letters;2024-01-18

4. Stereodivergent Construction of Contiguous Quaternary Carbon Centers Enabled by Asymmetric Catalysis;ACS Catalysis;2023-11-06

5. Total Synthesis of Tetracyclic Spirooxindole Alkaloids via a Double Oxidative Rearrangement/Cyclization Cascade;2023-09-20