16209-52-2Relevant articles and documents
Synthetic studies of decursivine derivatives: Preparation of key indole alkaloids via α-hydroxyalkylation
Ito, Fumihiro,Yamaguchi, Kentaro
, p. 3708 - 3716 (2012/06/30)
2-Hydroxyacetyl indole modified at C-3 position was prepared with an eye to developing a total synthesis of decursivine derivatives (decursivine, serotobenine, moschaminindolol, and flavumindole). The indole was prepared through a sequence of oxalyl chlor
Concise and diversity-oriented route toward polysubstituted 2-aminoimidazole alkaloids and their analogues
Ermolat'Ev, Denis S.,Bariwal, Jitender B.,Steenackers, Hans P. L.,De Keersmaecker, Sigrid C. J.,Van Der Eycken, Erik V.
supporting information; experimental part, p. 9465 - 9468 (2011/02/28)
Alkaloids of the naamine family were synthesized from diverse propargylamines in just two steps (see scheme: R1=Me, R 2=substituted benzyl, R3=Ar). Thus, the addition to a propargylamine of a carbodiimide generated in situ
An efficient and facile synthesis of capsaicin-like compounds as agonists of the TRPV1 receptor
Tran, Van H.,Kantharaj, Ravi,Roufogalis, Basil D.,Duke, Colin C.
, p. 2970 - 2976 (2007/10/03)
A new versatile synthetic route is described for the preparation of capsaicin-like molecules which contain an α-hydroxy ketone functional group mimicking the amide functional group in the capsaicin structure. The key reaction in this synthesis was the formation of α-(dimethylamino) alkanenitriles as intermediates. These nitriles were successfully prepared from both aliphatic and aromatic aldehydes by reaction with dimethylamine and aqueous sodium cyanide. Treatment of the nitriles with lithium diisopropylamide (LDA) followed by reaction with various aldehydes led to the formation of α-hydroxy ketone compounds, examples of which include 2-hydroxy-1-(4- hydroxy-3-methoxyphenyl)dodecan-3-one, (5R)- and (5S)-2-hydroxy-1-(4-hydroxy-3- methoxyphenyl)-5,9-dimethyldec-8-en-3-one, representing novel capsaicin-like molecules. Formation of (4-benzyloxy-3-methoxyphenyl)-acetaldehyde was also described from the Wittig reaction of 4-benzyloxy-3-methoxybenzadehyde with an ylide reagent (methoxymethyl)triphenylphosphonium bromide followed by acid hydrolysis to form the title compound. This aldehyde represents a useful precursor for the synthesis of capsaicin-like structures. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
