35478-77-4Relevant academic research and scientific papers
A catalytic versus stoichiometric photoinduced electron transfer promoted selective C16-C21 bond cleavage of catharanthine
Cocquet, Guillaume,Rool, Patrice,Ferroud, Clotilde
, p. 839 - 841 (2001)
A clean and efficient access to the cleavamine skeleton is described through the selective oxidative C16-C21 bond cleavage of catharanthine. The best result is obtained by the use of catalytic quantities of β-lapachone as photosensitizer, which permits the successful control of competition between the back electron transfer, the deprotonation and the fragmentation pathway.
Synthesis of (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine enabled by photoredox catalysis in flow
Beatty, Joel W.,Stephenson, Corey R. J.
, p. 10270 - 10273 (2014/08/05)
Natural product modification with photoredox catalysis allows for mild, chemoselective access to a wide array of related structures in complex areas of chemical space, providing the possibility for novel structural motifs as well as useful quantities of less abundant congeners. While amine additives have been used extensively as stoichiometric electron donors for photocatalysis, the controlled modification of amine substrates through single-electron oxidation is ideal for the synthesis and modification of alkaloids. Here, we report the conversion of the amine (+)-catharanthine into the natural products (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine utilizing visible light photoredox catalysis.
Selective deoxygenation of leurosine: Concise access to anhydrovinblastine
Hardouin, Christophe,Doris, Eric,Rousseau, Bernard,Mioskowski, Charles
, p. 6571 - 6574 (2007/10/03)
Straightforward access to anhydrovinblastine starting from the parent alkaloid leurosine is reported. The key deoxygenation step was first optimized on a model substrate. However, applied to leurosine, only the low-valent CP2TiCl gave satisfactory results.
Mechanistic Aspects of the Formation of Anhydrovinblasine by Potier-Polonovski Oxidative Coupling of Catharanthine and Vindoline. Spectroscopic Observation and Chemical Reactions of Intermediates
Sundberg, Richard J.,Gadamasetti, Kumar G.,Hunt, Phyllis J.
, p. 277 - 296 (2007/10/02)
The fragmentation-coupling of catharanthine and vindoline by trifluoroacetic anhydride has been carried out under conditions which allow observation of intermediates and comparison of the reactivity by low temperature NMR.These studies have been confirmed
PREPARATION OF 15-OXO-16-METHOXYCARBONYL-15,20-DIHYDRO-CLEAVAMINE AND COUPLING REACTION WITH VINDOLINE
Andriamialisoa, Ratremaniaina Z.,Langlois, Nicole,Langlois, Yves
, p. 245 - 250 (2007/10/02)
Several derivatives of 16-methoxycarbonyl cleavamines oxygenated in position 15 have been prepared and the coupling reaction of 15-oxo 16S-methoxycarbonyl 15,20-dihydro cleavamine with vindoline has been studied.
