Issue 1, 2016

Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation

Abstract

An efficient stereoselective synthesis of the nuphar alkaloid, (−)-nupharamine, is reported. The key features include the Lewis acid catalyzed reaction of an α-chlorosulfide with a silyl ketene acetal for C–C bond formation, creation of the stereocenter at C2 by a diastereoselective reaction of allyl indium with a sulfinimine and reductive amination for the introduction of the C6 stereocenter of the piperidine ring.

Graphical abstract: Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation

Supplementary files

Article information

Article type
Paper
Submitted
21 Aug 2015
Accepted
13 Oct 2015
First published
14 Oct 2015

Org. Biomol. Chem., 2016,14, 131-137

Author version available

Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation

S. Raghavan and S. Rajendar, Org. Biomol. Chem., 2016, 14, 131 DOI: 10.1039/C5OB01750E

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