Stereoselective total synthesis of (−)-nupharamine utilizing an α-chlorosulfide and a sulfinimine for C–C bond formation†,10.1039/C5OB01750E

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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

Sadagopan Raghavan,Sheelamanthula Rajendar

Organic & Biomolecular Chemistry Pub Date : 10/14/2015 00:00:00 , DOI:10.1039/C5OB01750E

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.