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Ruthenium Catalyzed Tandem Pictet-Spengler Reaction.
Nalikezhathu, Anju; Cherepakhin, Valeriy; Williams, Travis J.
Affiliation
  • Nalikezhathu A; Donald P. and Katherine B. Loker Hydrocarbon Institute and Department of Chemistry, University of Southern California, Los Angeles California 90089-1661, United States.
  • Cherepakhin V; Donald P. and Katherine B. Loker Hydrocarbon Institute and Department of Chemistry, University of Southern California, Los Angeles California 90089-1661, United States.
  • Williams TJ; Donald P. and Katherine B. Loker Hydrocarbon Institute and Department of Chemistry, University of Southern California, Los Angeles California 90089-1661, United States.
Org Lett ; 22(13): 4979-4984, 2020 07 02.
Article in En | MEDLINE | ID: mdl-32558575
ABSTRACT
We report a pyridyl-phosphine ruthenium(II) catalyzed tandem alcohol amination/Pictet-Spengler reaction sequence to synthesize tetrahydro-ß-carbolines from an alcohol and tryptamine. Our conditions use a Lewis acid cocatalyst, In(OTf)3, that is compatible with typically base catalyzed amination and an acid catalyzed Pictet-Spengler cyclization. This method proceeds well with benzylic alcohols, heterocyclic carbinols, and aliphatic alcohols. We also show how combining this reaction with a subsequent cycloamination enables a direct synthesis of tetracyclic alkaloids like harmicine.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Ruthenium Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Document type: Article Affiliation country: United States
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Ruthenium Language: En Journal: Org Lett Journal subject: BIOQUIMICA Year: 2020 Document type: Article Affiliation country: United States