Total synthesis of pipecolic acid and 1-C-alkyl 1,5-iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal-Reference-Cited by-同舟云学术

Total synthesis of pipecolic acid and 1-C-alkyl 1,5-iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal

Published:2018 Issue:7 Volume:16 Page:1118-1125
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Baś Sebastian¹²³⁴^ORCID,Kusy Rafał¹²³⁴,Pasternak-Suder Monika¹²³⁴,Nicolas Cyril⁵⁶⁷⁸⁹^ORCID,Mlynarski Jacek¹²³⁴¹⁰^ORCID,Martin Olivier R.⁵⁶⁷⁸⁹^ORCID

Affiliation:

1. Faculty of Chemistry

2. Jagiellonian University

3. 30-387 Krakow

4. Poland

5. Institut de Chimie Organique et Analytique

6. UMR CNRS 7311

7. Université d'Orléans

8. 45067 Orléans cedex 2

9. France

10. Institute of Organic Chemistry

Abstract

Asymmetric synthesis of the iminosugar moietyviadiastereoselective aldol addition of a pyruvate, a range of hydroxyketones and (S)-isoserinal, followed by catalytic reductive intramolecular amination.

Funder

Narodowe Centrum Nauki

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2018/OB/C7OB02797D

Reference49 articles.

1. Iminosugars: From Synthesis to Therapeutic Applications , ed. P. Compain and O. R. Martin , John Wiley & Sons , Chichester, England , 2007

2. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond , ed. A. E. Stutz , Wiley-VCH , Weinheim, Germany , 1999

3. Novel oral treatment of Gaucher's disease with N-butyldeoxynojirimycin (OGT 918) to decrease substrate biosynthesis

4. E. Fattorusso and O. T.Scafati , Modern Alkaloids , Wiley-VCH , New York , 2008 , p. 111

5. Glycosidase inhibitors: update and perspectives on practical use

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