Synthesis 2015; 47(23): 3673-3686
DOI: 10.1055/s-0035-1560174
paper
© Georg Thieme Verlag Stuttgart · New York

Diastereoselective Synthesis of Novel and Enantiopure Tetrahydropyrano[3,2-c]quinolines

Paseka T. Moshapo
Department of Chemistry, University of Johannesburg, P O Box 524, Auckland Park, South Africa   Email: hhkinfe@uj.ac.za
,
Henok H. Kinfe*
Department of Chemistry, University of Johannesburg, P O Box 524, Auckland Park, South Africa   Email: hhkinfe@uj.ac.za
› Author Affiliations
Further Information

Publication History

Received: 25 May 2015

Accepted after revision: 23 July 2015

Publication Date:
27 August 2015 (eFirst)

Abstract

Diastereoselective synthesis of novel and enantiopure N-alkylated tetrahydropyrano[3,2-c]quinolines is described via intramolecular Friedel–Crafts alkylation using a 1-O-acetylglucosyl derivative as the key intermediate. Unprecedented formation of new glycal derivatives and α,β-unsaturated carbaldehyde products is also discussed.

Supporting Information

 
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