Literature DB >> 32528190

Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy.

Cassandra L Schrank1,2, Michael W Danneman1, Emily A Prebihalo1, Robert E Anderson1, Tyler J Gibson1, William M Wuest2, Richard J Mullins1.   

Abstract

In recent work, asymmetric conjugate addition reactions to chiral 4-phenyl-N-enoyl-1,3-oxazolidinones have been shown to give different stereochemical outcomes depending on the conditions employed. Through the application of stereodivergent reaction conditions, the total synthesis of (+)-pilosinine and the formal synthesis of (-)-pilosinine has been completed from a single enantiomer of the 1,3-oxazolidi-none auxiliary.

Entities:  

Keywords:  Allylstannanes; Conjugate addition; Oxazolidinone; Pilosinine; Stereodivergent

Year:  2020        PMID： 32528190      PMCID： PMC7288726          DOI： 10.1016/j.tetlet.2020.151945

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  16 in total

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3.  Studies on the mode of action of pilocarpine on aqueous outflow.

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Authors:  David R Williams; Khalida Shamim
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

6.  Synthesis and biological activity of the C'D'E'F' ring system of maitotoxin.

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Authors:  Hiroki Kaneko; Shunsuke Takahashi; Noriyuki Kogure; Mariko Kitajima; Hiromitsu Takayama
Journal:  J Org Chem       Date:  2019-04-09       Impact factor: 4.354

9.  Leucascandrolide A: a second generation formal synthesis.

Authors:  David R Williams; Samarjit Patnaik; Scott V Plummer
Journal:  Org Lett       Date:  2003-12-25       Impact factor: 6.005

10.  Biogenetically inspired total syntheses of Lycopodium alkaloids, (+)-flabellidine and (-)-lycodine.

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Journal:  J Am Chem Soc       Date:  2014-08-11       Impact factor: 15.419
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