Literature DB >> 20175516

Total synthesis of (+/-)-powelline and (+/-)-buphanidrine.

Katherine M Bogle1, David J Hirst, Darren J Dixon.   

Abstract

The total synthesis of (+/-)-powelline (13 linear steps in an overall yield of 6%) and (+/-)-buphanidrine (14 linear steps and a 6% overall yield) and has been achieved using a novel approach to the crinane skeleton. An organocatalytic oxidative coupling allowed direct construction of the key quaternary carbon-to-aryl bond in high yield allowing rapid access to the target alkaloids.

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Year:  2010        PMID: 20175516     DOI: 10.1021/ol1000654

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


  3 in total

Review 1.  The Chemical Synthesis of the Crinine and Haemanthamine Alkaloids: Biologically Active and Enantiomerically-Related Systems that Serve as Vehicles for Showcasing New Methodologies for Molecular Assembly.

Authors:  Nan Hu; Lorenzo V White; Ping Lan; Martin G Banwell
Journal:  Molecules       Date:  2021-02-02       Impact factor: 4.411

Review 2.  Cupreines and cupreidines: an established class of bifunctional cinchona organocatalysts.

Authors:  Laura A Bryant; Rossana Fanelli; Alexander J A Cobb
Journal:  Beilstein J Org Chem       Date:  2016-03-07       Impact factor: 2.883

3.  Bioinspired enantioselective synthesis of crinine-type alkaloids via iridium-catalyzed asymmetric hydrogenation of enones.

Authors:  Xiao-Dong Zuo; Shu-Min Guo; Rui Yang; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2017-07-03       Impact factor: 9.825

  3 in total

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