934586-52-4Relevant academic research and scientific papers
A dipolar cycloaddition approach toward the kopsifoline alkaloid framework
Hong, Xuechuan,France, Stefan,Padwa, Albert
, p. 5962 - 5976 (2008/02/07)
Using a metal-catalyzed domino reaction as the key step, the heterocyclic skeleton of the kopsifoline alkaloid family was constructed by a 1,3-dipolar cycloaddition of a carbonyl ylide dipole derived from a Rh(II)-catalyzed reaction of a diazo ketoester across the indole π-bond. Ring opening of the resulting 1,3-dipolar cycloadduct followed by a reductive dehydroxylation step resulted in the formation of a critical silyl enol ether necessary for the final F-ring closure of the kopsifoline skeleton.
Rhodium carbenoid induced cycloadditions of diazo ketoimides across indolyl π-bonds
Hong, Xuechuan,Mejía-Oneto, José M.,France, Stefan,Padwa, Albert
, p. 775 - 779 (2007/12/27)
A series of diazo ketoimides prepared from (1H-indol-3-yl)acetyl chloride and alkyl 2-diazo-3-(3-substituted-2-oxopiperidin-3-yl)-3-oxopropanoates were treated with rhodium(II) acetate. Attack of the imido carbonyl oxygen at the resultant rhodium carbenoi
Cycloaddition protocol for the assembly of the hexacyclic framework associated with the kopsifoline alkaloids
Hong, Xuechuan,France, Stefan,Mejia-Oneto, Jose M.,Padwa, Albert
, p. 5141 - 5144 (2007/10/03)
(Chemical Equation Presented) An approach to the hexacyclic framework of the kopsifoline alkaloids has been developed and is based on a Rh(II)-catalyzed cyclization-cycloaddition cascade. The resulting [3+2]-cycloadduct was readily converted into the TBS
