Literature DB >> 29155468

Gram-Scale Synthesis of the (-)-Sparteine Surrogate and (-)-Sparteine.

James D Firth1, Steven J Canipa1, Leigh Ferris2, Peter O'Brien1.   

Abstract

An 8-step, gram-scale synthesis of the (-)-sparteine surrogate (22 % yield, with just 3 chromatographic purifications) and a 10-step, gram-scale synthesis of (-)-sparteine (31 % yield) are reported. Both syntheses proceed with complete diastereocontrol and allow access to either antipode. Since the syntheses do not rely on natural product extraction, our work addresses long-term supply issues relating to these widely used chiral ligands.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkaloids; asymmetric synthesis; kinetic resolution; nitrogen ligands; total synthesis

Year:  2017        PMID： 29155468     DOI： 10.1002/anie.201710261

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


  3 in total

Review 1.  The role of biocatalysis in the asymmetric synthesis of alkaloids - an update.

Authors:  Emmanuel Cigan; Bettina Eggbauer; Joerg H Schrittwieser; Wolfgang Kroutil
Journal:  RSC Adv       Date:  2021-08-20       Impact factor: 3.361

2.  Sustainable Asymmetric Organolithium Chemistry: Enantio- and Chemoselective Acylations through Recycling of Solvent, Sparteine, and Weinreb "Amine".

Authors:  Serena Monticelli; Wolfgang Holzer; Thierry Langer; Alexander Roller; Berit Olofsson; Vittorio Pace
Journal:  ChemSusChem       Date:  2019-02-13       Impact factor: 8.928

3.  Regiodivergent enantioselective C-H functionalization of Boc-1,3-oxazinanes and application to the synthesis of β2 and β3-amino acids.

Authors:  Weilong Lin; Ke-Feng Zhang; Olivier Baudoin
Journal:  Nat Catal       Date:  2019-09-09
  3 in total

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