Publication:
A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives

Issued Date

2007-11-12

Resource Type

Article

ISSN

00404039

DOI

10.1016/j.tetlet.2007.09.073

Other identifier(s)

2-s2.0-35348838923

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron Letters. Vol.48, No.46 (2007), 8182-8184

Suggested Citation

Chutima Kuhakarn, Nattakan Panyachariwat, Somsak Ruchirawat A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives. Tetrahedron Letters. Vol.48, No.46 (2007), 8182-8184. doi:10.1016/j.tetlet.2007.09.073 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/24083

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Title

A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives

Author(s)

Chutima Kuhakarn
 Nattakan Panyachariwat
 Somsak Ruchirawat

Other Contributor(s)

Chulabhorn Research Institute
 Mahidol University

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.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/24083

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Scopus 2006-2010