Literature DB >> 28474489

Asymmetric Total Syntheses of (-)-α-Lycorane, (-)-Zephyranthine, and Formal Synthesis of (+)-Clivonine.

Yong-Jian Chen1, Sen-Lin Cai1, Chuan-Chuan Wang1, Jin-Duo Cheng1, Søren Kramer2, Xing-Wen Sun1.   

Abstract

An asymmetric route to (-)-α-lycorane and (-)-zephyranthine, and a formal total synthesis of (+)-clivonine were achieved. A pivotal intermediate, which serves as a potent precursor for the divergent syntheses of these natural products, was accessed by a diastereoselective Pd-catalyzed cinnamylation of an N-tert-butanesulfinyl imine.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; asymmetric synthesis; total synthesis; zephyranthine; α-lycorane

Mesh:

Substances:

Year:  2017        PMID: 28474489     DOI: 10.1002/asia.201700555

Source DB:  PubMed          Journal:  Chem Asian J        ISSN: 1861-471X


  4 in total

1.  Hydroamination of Dihapto-Coordinated Benzene and Diene Complexes of Tungsten: Fundamental Studies and the Synthesis of γ-Lycorane.

Authors:  Katy B Wilson; Hannah S Nedzbala; Spenser R Simpson; Megan N Ericson; Karl S Westendorff; Mahendra D Chordia; Diane A Dickie; W Dean Harman
Journal:  Helv Chim Acta       Date:  2021-08-10       Impact factor: 2.164

Review 2.  Applications of tert-butanesulfinamide in the synthesis of N-heterocycles via sulfinimines.

Authors:  Rose Mary Philip; Sankaran Radhika; P V Saranya; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2020-11-23       Impact factor: 4.036

3.  Transannular Approach to 2,3-Dihydropyrrolo[1,2-b]isoquinolin-5(1H)-ones through Brønsted Acid-Catalyzed Amidohalogenation.

Authors:  Estefanía Capel; Javier Luis-Barrera; Ana Sorazu; Uxue Uria; Liher Prieto; Efraím Reyes; Luisa Carrillo; Jose L Vicario
Journal:  J Org Chem       Date:  2022-07-26       Impact factor: 4.198

4.  Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

Authors:  Yuxiang Zhao; Yanren Zhu; Guolan Ma; Qi Wei; Shaoxiong Yang; Xiaoyu Zeng; Hongbin Zhang; Jingbo Chen
Journal:  Chem Sci       Date:  2021-06-21       Impact factor: 9.825

  4 in total

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