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

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 metho...

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Main Authors:	Chutima Kuhakarn, Nattakan Panyachariwat, Somsak Ruchirawat
Other Authors:	Chulabhorn Research Institute
Format:	Article
Published:	2018
Subjects:	Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics
Online Access:	https://repository.li.mahidol.ac.th/handle/123456789/24083
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Institution:	Mahidol University

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spelling	th-mahidol.240832018-08-24T09:14:11Z A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives Chutima Kuhakarn Nattakan Panyachariwat Somsak Ruchirawat Chulabhorn Research Institute Mahidol University Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics 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. 2018-08-24T01:39:29Z 2018-08-24T01:39:29Z 2007-11-12 Article Tetrahedron Letters. Vol.48, No.46 (2007), 8182-8184 10.1016/j.tetlet.2007.09.073 00404039 2-s2.0-35348838923 https://repository.li.mahidol.ac.th/handle/123456789/24083 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=35348838923&origin=inward
institution	Mahidol University
building	Mahidol University Library
continent	Asia
country	Thailand Thailand
content_provider	Mahidol University Library
collection	Mahidol University Institutional Repository
topic	Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics
spellingShingle	Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics 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
description	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.
author2	Chulabhorn Research Institute
author_facet	Chulabhorn Research Institute Chutima Kuhakarn Nattakan Panyachariwat Somsak Ruchirawat
format	Article
author	Chutima Kuhakarn Nattakan Panyachariwat Somsak Ruchirawat
author_sort	Chutima Kuhakarn
title	A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
title_short	A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
title_full	A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
title_fullStr	A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
title_full_unstemmed	A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
title_sort	variation of the pictet-spengler reaction via a sequential reduction-cyclization reaction of n-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives
publishDate	2018
url	https://repository.li.mahidol.ac.th/handle/123456789/24083
_version_	1763489645999423488

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

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