Literature DB >> 22612349

Total synthesis of (-)-galanthamine and (-)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization.

Ji-Qiang Chen1, Jian-Hua Xie, Deng-Hui Bao, Sheng Liu, Qi-Lin Zhou.   

Abstract

A synthetic strategy featuring efficient ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryloxy cyclic ketone via dynamic kinetic resolution and palladium-catalyzed intramolecular reductive Heck cyclization has been developed for the asymmetric total synthesis of (-)-galanthamine (20.1%, 12 steps) and (-)-lycoramine (40.2%, 10 steps).

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Year:  2012        PMID： 22612349     DOI： 10.1021/ol300913g

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


  6 in total

1.  Accelerating the semisynthesis of alkaloid-based drugs through metabolic engineering.

Authors:  Amy M Ehrenworth; Pamela Peralta-Yahya
Journal:  Nat Chem Biol       Date:  2017-02-15       Impact factor: 15.040

2.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

3.  Palladium-Catalyzed Reductive Heck Coupling of Alkenes.

Authors:  Lucas J Oxtoby; John A Gurak; Steven R Wisniewski; Martin D Eastgate; Keary M Engle
Journal:  Trends Chem       Date:  2019-06-20

4.  Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure.

Authors:  Yang Liu; Li-Jie Cheng; Hai-Tao Yue; Wen Che; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2016-04-12       Impact factor: 9.825

5.  Amaryllidaceae Alkaloids of Belladine-Type from Narcissus pseudonarcissus cv. Carlton as New Selective Inhibitors of Butyrylcholinesterase.

Authors:  Abdullah Al Mamun; Jana Maříková; Daniela Hulcová; Jiří Janoušek; Marcela Šafratová; Lucie Nováková; Tomáš Kučera; Martina Hrabinová; Jiří Kuneš; Jan Korábečný; Lucie Cahlíková
Journal:  Biomolecules       Date:  2020-05-22

6.  Amaryllidaceae Alkaloids of Different Structural Types from Narcissus L. cv. Professor Einstein and Their Cytotoxic Activity.

Authors:  Kateřina Breiterová; Darja Koutová; Jana Maříková; Radim Havelek; Jiří Kuneš; Martina Majorošová; Lubomír Opletal; Anna Hošťálková; Jaroslav Jenčo; Martina Řezáčová; Lucie Cahlíková
Journal:  Plants (Basel)       Date:  2020-01-22
  6 in total

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