Literature DB >> 21966984

Asymmetric aziridination of cyclic enones using chiral diamine catalysts and its application to the total synthesis of (-)-agelastatin A.

Yasuhiro Menjo1, Akinari Hamajima, Neri Sasaki, Yasumasa Hamada.   

Abstract

The asymmetric aziridination of cyclic enones with N-tosyloxycarbamates, using N-neopentyl 1,2-diphenylethylenediamine as a catalyst, and its application to the formal total synthesis of (-)-agelastatin A, using a one-pot silylation-selenylation procedure and the regioselective aziridine-opening by an azide anion as key steps, are described.
© 2011 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21966984     DOI： 10.1021/ol2023054

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

2.  Synthesis and Evaluation of Agelastatin Derivatives as Potent Modulators for Cancer Invasion and Metastasis.

Authors:  Alyssa H Antropow; Kun Xu; Rachel J Buchsbaum; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2017-07-25       Impact factor: 4.354

3.  CuH-Catalyzed Regioselective Intramolecular Hydroamination for the Synthesis of Alkyl-Substituted Chiral Aziridines.

Authors:  Haoxuan Wang; Jeffrey C Yang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-06-15       Impact factor: 15.419

4.  Bioinspired total synthesis of agelastatin A.

Authors:  Jeremy Chris P Reyes; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-11       Impact factor: 15.336

5.  Synthesis and anticancer activity of all known (-)-agelastatin alkaloids.

Authors:  Sunkyu Han; Dustin S Siegel; Karen C Morrison; Paul J Hergenrother; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2013-11-21       Impact factor: 4.354

6.  Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine.

Authors:  Susanna K Maisto; Angela P Leersnyder; Gwyneth L Pudner; Jonathan R Scheerer
Journal:  J Org Chem       Date:  2020-06-30       Impact factor: 4.354

7.  Efficient Access to Chiral Trisubstituted Aziridines via Catalytic Enantioselective Aza-Darzens Reactions.

Authors:  Barry M Trost; Tanguy Saget; Chao-I Joey Hung
Journal:  Angew Chem Int Ed Engl       Date:  2017-01-23       Impact factor: 15.336

8.  Synthesis of Agelastatin A and Derivatives Premised on a Hidden Symmetry Element Leading to Analogs Displaying Anticancer Activity.

Authors:  Haoran Xue; Haleigh Svatek; Ariane F Bertonha; Keighley Reisenauer; Joshua Robinson; Minwoo Kim; Alec Ingros; Matthew Ho; Joseph Taube; Daniel Romo
Journal:  Tetrahedron       Date:  2021-07-10       Impact factor: 2.388

Review 9.  Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Authors:  Xiao Wang; Zhiqiang Ma; Xiaolei Wang; Saptarshi De; Yuyong Ma; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-05-15       Impact factor: 6.222

10.  Formal synthesis of (-)-agelastatin A: an iron(II)-mediated cyclization strategy.

Authors:  Daisuke Shigeoka; Takuma Kamon; Takehiko Yoshimitsu
Journal:  Beilstein J Org Chem       Date:  2013-05-03       Impact factor: 2.883
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.