Total Synthesis of Unsymmetrically Oxidized Nuphar Thioalkaloids via Copper-Catalyzed Thiolane Assembly

An asymmetric total synthesis of (+)-6-hydroxy­thio­binupharidine (1b) and (−)-6-hydroxy­thio­nuphlutine (2b), a set of hemiaminal containing dimeric sesquiterpenes isolated from yellow water lilies of the Nuphar genus, is described. The central bis-spirocyclic tetrahydro­thiophene ring was forged t...

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Veröffentlicht in:	Journal of the American Chemical Society 2017-09, Vol.139 (38), p.13272-13275
Hauptverfasser:	Lacharity, Jacob J, Fournier, Jeremy, Lu, Ping, Mailyan, Artur K, Herrmann, Aaron T, Zakarian, Armen
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemistry Catalysis Copper - chemistry dimerization Nuphar Nuphar - chemistry oxidation Oxidation-Reduction Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Sesquiterpenes - isolation & purification sesquiterpenoids water lilies
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