Issue 45, 2013

A diastereoselective route to 2,5-diaryl-3,4-disubstituted tetrahydrofuran lignans: protection free synthesis of (+)-galbelgin and (+)-galbacin

Abstract

An efficient and protection free asymmetric synthesis has been reported for all-trans variant 2,5-diaryl-3,4-disubstituted tetrahydrofuran lignans in seven steps from N-succinyl-2-oxazolidinone. (+)-Galbelgin and (+)-galbacin were synthesized in very good overall yields by this route where diastereoselective aldol reaction, stereoselective C-alkylation over O-alkylation and Friedel–Crafts reaction serve as key steps.

Graphical abstract: A diastereoselective route to 2,5-diaryl-3,4-disubstituted tetrahydrofuran lignans: protection free synthesis of (+)-galbelgin and (+)-galbacin

Supplementary files

Article information

Article type
Communication
Submitted
22 Aug 2013
Accepted
25 Sep 2013
First published
26 Sep 2013

RSC Adv., 2013,3, 22834-22836

A diastereoselective route to 2,5-diaryl-3,4-disubstituted tetrahydrofuran lignans: protection free synthesis of (+)-galbelgin and (+)-galbacin

S. Hazra and S. Hajra, RSC Adv., 2013, 3, 22834 DOI: 10.1039/C3RA44573A

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