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Structure elucidation and stereoselective total synthesis of pavettamine, the causal agent of gousiekte
Authors:Moira L. Bode  Samson Y. Gebretnsae
Affiliation:a Discovery Chemistry, CSIR Biosciences, Private Bag X2, Modderfontein 1645, South Africa
b Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, United Kingdom
c Department of Chemistry, University of Pretoria, Lynnwood Road, Hillcrest, Pretoria 0002, South Africa
Abstract:The structure elucidation of a novel natural product pavettamine (1), the causal agent of the plant toxicosis gousiekte, is reported. The structure was defined by analysis of NMR and MS data and the relative configuration followed from the 13C NMR data of the acetonide derivative. The absolute stereochemistry was established by total synthesis from (2S)-malic acid using chiral sulfoxide methodology as (2S,4R,8R,10S)-1,11-diamino-6-aza-undecane-2,4,8,10-tetraol.
Keywords:Pavettamine   Gousiekte   Stereoselective synthesis   Polyamine   Pavetta harborii   β-Ketosulfoxide reduction
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