Literature DB >> 25080299

Catalytic asymmetric Torgov cyclization: a concise total synthesis of (+)-estrone.

Sébastien Prévost1, Nathalie Dupré, Markus Leutzsch, Qinggang Wang, Vijay Wakchaure, Benjamin List.   

Abstract

An asymmetric Torgov cyclization, catalyzed by a novel, highly Brønsted acidic dinitro-substituted disulfonimide, is described. The reaction delivers the Torgov diene and various analogues with excellent yields and enantioselectivity. This method was applied in a very short synthesis of (+)-estrone.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  disulfonimides; estrone; organocatalysis; torgov cyclization; total synthesis

Mesh：

Substances：

Year:  2014        PMID： 25080299     DOI： 10.1002/anie.201404909

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


  8 in total

1.  Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation.

Authors:  Hem Raj Khatri; Bijay Bhattarai; Will Kaplan; Zhongzheng Li; Marcus John Curtis Long; Yimon Aye; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2019-03-14       Impact factor: 15.419

2.  Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

Authors:  Hem Raj Khatri; Nolan Carney; Ryan Rutkoski; Bijay Bhattarai; Pavel Nagorny
Journal:  European J Org Chem       Date:  2020-01-01

3.  Concise Enantioselective Synthesis of Oxygenated Steroids via Sequential Copper(II)-Catalyzed Michael Addition/Intramolecular Aldol Cyclization Reactions.

Authors:  Nathan R Cichowicz; Will Kaplan; Yaroslav Khomutnyk; Bijay Bhattarai; Zhankui Sun; Pavel Nagorny
Journal:  J Am Chem Soc       Date:  2015-11-10       Impact factor: 15.419

4.  Brønsted acid-promoted hydroamination of unsaturated hydrazones: access to biologically important 5-arylpyrazolines.

Authors:  Han He; Ning Xu; Honglin Zhang; Bin Chen; Zhengnan Hu; Kang Guo; Jianlin Chun; Shujun Cao; Yingguang Zhu
Journal:  RSC Adv       Date:  2021-05-11       Impact factor: 4.036

5.  Forging Fluorine-Containing Quaternary Stereocenters by a Light-Driven Organocatalytic Aldol Desymmetrization Process.

Authors:  Sara Cuadros; Luca Dell'Amico; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-18       Impact factor: 15.336

6.  A convergent total synthesis of ouabagenin.

Authors:  Ken Mukai; Satoshi Kasuya; Yuki Nakagawa; Daisuke Urabe; Masayuki Inoue
Journal:  Chem Sci       Date:  2015-03-30       Impact factor: 9.825

7.  Disulfonimides versus Phosphoric Acids in Brønsted Acid Catalysis: The Effect of Weak Hydrogen Bonds and Multiple Acceptors on Complex Structures and Reactivity.

Authors:  Kerstin Rothermel; Matej Žabka; Johnny Hioe; Ruth M Gschwind
Journal:  J Org Chem       Date:  2019-10-02       Impact factor: 4.354

8.  Desymmetrization of unactivated bis-alkenes via chiral Brønsted acid-catalysed hydroamination.

Authors:  Zhang-Long Yu; Yong-Feng Cheng; Na-Chuan Jiang; Jian Wang; Li-Wen Fan; Yue Yuan; Zhong-Liang Li; Qiang-Shuai Gu; Xin-Yuan Liu
Journal:  Chem Sci       Date:  2020-05-20       Impact factor: 9.825
  8 in total

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