Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 26, Pages 7440-7443Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201703178
Keywords
alkaloids; asymmetric catalysis; heterocycles; organocatalysis; total synthesis
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Funding
- National Key R&D Program of China [2016YFA0202900]
- National Basic Research Program of China [2015CB856600]
- NSFC [21332009, 21361140373, 21421091]
- Program of Shanghai Subject Chief Scientist [16XD1404300]
- CAS [XDB20000000, QYZDY-SSW-SLH012]
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A highly efficient synthesis of the enantioenriched tetrahydro-beta-carbolines was developed by using a chiral phosphoric acid catalyzed Pictet-Spengler reaction of indolyl dihydropyridines. The reaction proceeds under mild reaction conditions to afford the desired chiral tetrahydro-b-carbolines in good to excellent yields (up to 96%) and high enantio-selectivities (up to 99% ee). With this method, a formal synthesis of tangutorine and a total synthesis of deplancheine were achieved in a highly efficient manner.
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