title: Collective synthesis of natural products by means of organocascade catalysis.
abstract: Organic chemists are now able to synthesize small quantities of almost any known natural product, given sufficient time, resources and effort. However, translation of the academic successes in total synthesis to the large-scale construction of complex natural products and the development of large collections of biologically relevant molecules present significant challenges to synthetic chemists. Here we show that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold. The power of this concept has been demonstrated through the expedient, asymmetric total syntheses of six well-known alkaloid natural products: strychnine, aspidospermidine, vincadifformine, akuammicine, kopsanone and kopsinine.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Spencer B
authors.initials: SB
authors.lastname: Jones
authors.forename: Bryon
authors.initials: B
authors.lastname: Simmons
authors.forename: Anthony
authors.initials: A
authors.lastname: Mastracchio
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry; D012107:Research Design; D013331:Strychnine / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000470:Alkaloids; D001688:Biological Products; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; C409672:aspidospermidine; C456406:vincadifformine; C061491:kopsinine; D013331:Strychnine; C434103:akuammicine