289906-69-0Relevant academic research and scientific papers
Pd-catalyzed assembly of spirooxindole natural products: A short synthesis of horsfiline
Deppermann, Nina,Thomanek, Heike,Prenzel, Alexander H. G. P.,Maison, Wolfgang
experimental part, p. 5994 - 6000 (2010/12/19)
The Pd-catalyzed intramolecular α-arylation of amides is applied to the synthesis of functionalized spirooxindoles. The substrate scope is evaluated, and the reaction is demonstrated to be useful for the assembly of spirooxindole natural products and derivatives thereof. As an application, a new synthesis of horsfiline 1 is presented, giving the natural product in only 4 steps from commercially available amino acid 12.
Applications of NHC-mediated O- to C-carboxyl transfer: synthesis of (±)-N-benzyl-coerulescine and (±)-horsfiline
Thomson, Jennifer E.,Kyle, Andrew F.,Ling, Kenneth B.,Smith, Siobhan R.,Slawin, Alexandra M.Z.,Smith, Andrew D.
experimental part, p. 3801 - 3813 (2010/07/02)
NHC-promoted O- to C-carboxyl transfer of 3-allyl indolyl phenyl carbonates generates 3-allyl-3-phenoxycarbonyl-oxindoles with good catalytic efficiency, which are readily converted into (±)-N-benzyl-coerulescine and (±)-horsfiline.
Concise synthesis of (±)-horsfiline and (±)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides
Lizos, Dimitrios E.,Murphy, John A.
, p. 117 - 122 (2007/10/03)
A brief, efficient and economical synthesis of the spiropyrrolidinyloxindoles, horsfiline and coerulescine, has been achieved, starting from itaconic acid and, respectively, p-anisidine or o-iodoaniline. Tandem radical cyclisation of iodoaryl alkenyl azides is the key step in both syntheses.
A novel and economical route to (±)-horsfiline using an aryl iodoazide tandem radical cyclisation strategy
Lizos,Tripoli,Murphy
, p. 2732 - 2733 (2007/10/03)
(±)-Horsfiline has been synthesised using a tandem radical cyclisation as the key step.
Efficient synthesis of (±)-horsfiline through the MgI2-catalyzed ring- expansion reaction of a spiro[cyclopropane-1,3'-indol]-2'-one
Fischer, Christian,Meyers, Christiane,Carreira, Erick M.
, p. 1175 - 1181 (2007/10/03)
We report a short synthetic route to (±)-horsfiline that provides the racemate in five steps from commercially available, substituted isatin in 41% overall yield. Efficient entry into the spiro[oxindole-pyrrolidine] ring system is possible through the application of the cyclopropane opening/ring expansion chemistry we have described with MgI2 as a bifunctional catalyst.
