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

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...

Full description

Saved in:
Bibliographic Details
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
Tags: Add Tag
No Tags, Be the first to tag this record!
Institution: Mahidol University
Description
Summary: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.

Similar Items