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Synthesis 2018; 50(05): 1113-1122
DOI: 10.1055/s-0036-1589523
DOI: 10.1055/s-0036-1589523
paper
Protecting-Group-Directed Regio- and Stereoselective Oxymercuration–Demercuration: Synthesis of Piperidine Alkaloids Containing 1,2- and 1,3-Amino Alcohol Units
Authors
This publication was supported by the Ministry of Education and Science of the Russian Federation (Agreement No. 02.А03.21.0008) and Council of Science and Research, New Delhi, project No. 02(252)/16/EMR-II.
Weitere Informationen
Publikationsverlauf
Received: 01. Juli 2017
Accepted after revision: 23. Oktober 2017
Publikationsdatum:
29. November 2017 (online)
Abstract
An efficient synthesis of naturally occurring 1,2- and 1,3-amino alcohol unit containing 2-substituted piperidine alkaloids and their analogues has been developed from l-pipecolinic acid. The protocol describes the regio- and stereoselective oxymercuration–demercuration of 2-alkenyl piperidines based on protecting groups to give piperidine alkaloids as a key step.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589137.
- Supporting Information (PDF)
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For 1,2-amino alcohols:
For 1,3-amino alcohols:
References for oxymercuration–demercuration reaction in natural product synthesis: