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Kokkonda P , Brown KR , Seguin TJ , Wheeler SE , Vaddypally S , Zdilla MJ , Andrade RB
Biomimetic Total Syntheses of (-)-Leucoridines A and C through the Dimerization of (-)-Dihydrovalparicine
Angew Chem Int Ed Engl. 2015 Oct 19;54(43) :12632-5
PMID: 26315453 URL: http://www.ncbi.nlm.nih.gov/pubmed/26315453
AbstractConcise 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.
NotesKokkonda, Praveen Brown, Keaon R Seguin, Trevor J Wheeler, Steven E Vaddypally, Shivaiah Zdilla, Michael J Andrade, Rodrigo B eng Germany 2015/09/01 06:00 Angew Chem Int Ed Engl. 2015 Oct 19;54(43):12632-5. doi: 10.1002/anie.201505198. Epub 2015 Aug 28.