16209-52-2Relevant academic research and scientific papers
Synthetic studies of decursivine derivatives: Preparation of key indole alkaloids via α-hydroxyalkylation
Ito, Fumihiro,Yamaguchi, Kentaro
experimental part, 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
A bismuth(III)-catalyzed friedel-crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin
Eey, Stanley T.-C.,Lear, Martin J.
, p. 5510 - 5513 (2011/03/18)
A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)3 to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promoted cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.
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
Asymmetric total synthesis of (-)-plicatic acid via a highly enantioselective and diastereoselective nucleophilic epoxidation of acyclic trisubstitued olefins
Sun, Bing-Feng,Hong, Ran,Kang, Yan-Biao,Deng, Li
supporting information; experimental part, p. 10384 - 10385 (2009/12/23)
(Chemical Equation Presented) The first total synthesis of (-)-plicatic acid has been achieved by a concise and enantioselective route. In this synthesis, a conceptually new strategy featuring an asymmetric epoxidation-intramolecular epoxy-ring-opening Friedel-Crafts reaction sequence was developed for the stereoselective construction of the 2,7′- cyclolignane skeleton bearing contiguous quaternary-quaternary-tertiary stereocenters. The implementation of this strategy was enabled by the development of a modified protocol for the Seebach epoxidation with TADOOH, which affords an unprecedented, highly enantioselective and diastereoselective epoxidation with a range of α-carbonyl-β-substituted acrylates 3.
PHENYLALKANOL COMPOUNDS
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Page/Page column 26; 28; 41; 42; 62, (2010/11/25)
The present invention relates to phenylalkanol compounds of formula (I) and derivatives, prodrugs, isomers and/or tautomers thereof. The present invention also relates to processes for the preparation of a compound of formula (I) and their use as pharmaceutical or veterinary agents, in particular as modulators of the vanilloid receptor for the treatment and/or prophylaxis of pain.
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.
Analogues of capsaicin with agonist activity as novel analgesic agents; structure-activity studies. 2. The amide bond 'B-region'
Walpole,Wrigglesworth,Bevan,Campbell,Dray,James,Masdin,Perkins,Winter
, p. 2373 - 2380 (2007/10/02)
A series of compounds incorporating replacements for the amide bond 'B- region' moiety of capsaicin have been synthesized, including vanillylamides and esters, homovanillic acid amides and esters, ureas, and thioureas. These have been tested in an in vitr
