7267-97-2Relevant academic research and scientific papers
Biomimetic total syntheses of (-)-leucoridines A and C through the dimerization of (-)-dihydrovalparicine
Kokkonda, Praveen,Brown, Keaon R.,Seguin, Trevor J.,Wheeler, Steven E.,Vaddypally, Shivaiah,Zdilla, Michael J.,Andrade, Rodrigo B.
supporting information, p. 12632 - 12635 (2015/10/28)
Concise biomimetic syntheses of the Strychnos-Strychnos-type bis-indole alkaloids (-)-leucoridine A (1) and C (2) were accomplished through the biomimetic dimerization of (-)-dihydrovalparicine (3). En route to 3, the known alkaloids (+)-geissoschizoline (8) and (-)-dehydrogeissoschizoline (10) were also prepared. DFT calculations were employed to elucidate the mechanism, which favors a stepwise aza-Michael/spirocyclization sequence over the alternate hetero-Diels-Alder cycloaddition reaction. Concise biomimetic syntheses of the Strychnos-Strychnos-type bis-indole alkaloids (-)-leucoridine A and C were accomplished through the biomimetic dimerization of (-)-dihydrovalparicine. DFT calculations were used to elucidate the mechanism, which favors a stepwise aza-Michael/spirocyclization sequence over the alternate hetero-Diels-Alder cycloaddition reaction.
