Biomimetic Total Syntheses of (−)-Leucoridines A and C through the Dimerization of (−)-Dihydrovalparicine
Praveen Kokkonda
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorKeaon R. Brown
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorTrevor J. Seguin
Department of Chemistry, Texas A & M University, College Station, TX 77843 (USA)
Search for more papers by this authorDr. Steven E. Wheeler
Department of Chemistry, Texas A & M University, College Station, TX 77843 (USA)
Search for more papers by this authorDr. Shivaiah Vaddypally
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorDr. Michael J. Zdilla
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorCorresponding Author
Dr. Rodrigo B. Andrade
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randradeSearch for more papers by this authorPraveen Kokkonda
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorKeaon R. Brown
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorTrevor J. Seguin
Department of Chemistry, Texas A & M University, College Station, TX 77843 (USA)
Search for more papers by this authorDr. Steven E. Wheeler
Department of Chemistry, Texas A & M University, College Station, TX 77843 (USA)
Search for more papers by this authorDr. Shivaiah Vaddypally
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorDr. Michael J. Zdilla
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Search for more papers by this authorCorresponding Author
Dr. Rodrigo B. Andrade
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade
Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randradeSearch for more papers by this authorAbstract
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.
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