title: Biomimetic Total Syntheses of (-)-Leucoridines A and C through the Dimerization of (-)-Dihydrovalparicine.
abstract: 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.
authors: Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade.
authors: Praveen
authors: P
authors: Kokkonda
authors: Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade.
authors: Keaon R
authors: KR
authors: Brown
authors: Department of Chemistry, Texas A & M University, College Station, TX 77843 (USA).
authors: Trevor J
authors: TJ
authors: Seguin
authors: Department of Chemistry, Texas A & M University, College Station, TX 77843 (USA).
authors: Steven E
authors: SE
authors: Wheeler
authors: Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade.
authors: Shivaiah
authors: S
authors: Vaddypally
authors: Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade.
authors: Michael J
authors: MJ
authors: Zdilla
authors: Department of Chemistry, Temple University, Philadelphia, PA 19122 (USA) https://www.cst.temple.edu/∼randrade. randrade@temple.edu.
authors: Rodrigo B
authors: RB
authors: Andrade
mesh_terms: D032701:Biomimetics / Q000379:methods; D061565:Cycloaddition Reaction / Q000379:methods; D019281:Dimerization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D019684:Magnoliopsida / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism
chemical_list: D026121:Indole Alkaloids
keywords: biomimetic synthesis; indole alkaloids; natural products; reaction mechanisms; total synthesis