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Please use this identifier to cite or link to this item: http://repository.li.mahidol.ac.th/dspace/handle/123456789/24083
Title: A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
Authors: Chutima Kuhakarn
Nattakan Panyachariwat
Somsak Ruchirawat
Chulabhorn Research Institute
Mahidol University
Keywords: Biochemistry, Genetics and Molecular Biology;Chemistry;Pharmacology, Toxicology and Pharmaceutics
Issue Date: 12-Nov-2007
Citation: Tetrahedron Letters. Vol.48, No.46 (2007), 8182-8184
Abstract: A new variation of the Pictet-Spengler reaction for the synthesis of 1-substituted tetrahydroisoquinoline derivatives has been developed. The reaction employs the reduction of N-acylcarbamates by DIBAL-H followed by simultaneous cyclization mediated by BF3·OEt2. The synthetic potential of this method has been illustrated by the synthesis of the tetrahydroisoquinoline alkaloids, (±)-xylopinine, (±)-laudanosine, (±)-8-oxo-O-methylbharatamine, and (±)-isoindoloisoquinolone. © 2007 Elsevier Ltd. All rights reserved.
URI: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=35348838923&origin=inward
http://repository.li.mahidol.ac.th/dspace/handle/123456789/24083
ISSN: 00404039
Appears in Collections:Scopus 2006-2010

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