title: Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol.
abstract: We have applied a diversity-oriented approach for the synthesis of skeletally diverse and stereochemically complex templates for small-molecule library production by performing Beckmann rearrangement and Beckmann fragmentation reactions on the bicyclo[3.2.1]octane rings of steviol and isosteviol, aglycones derived from the diterpene natural product stevioside. The optimization of these two reaction pathways is presented along with the successful application of a photo-Beckmann rearrangement. This work also led to the discovery of cyano-Prins-type and Thorpe-Ziegler-type cyclization reactions.
authors.affiliation: Institute for Therapeutics Discovery and Development, Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, 717 Delaware Street SE, Minneapolis, Minnesota 55414, United States.
authors.forename: Oliver E
authors.initials: OE
authors.lastname: Hutt
authors.forename: Trinh L
authors.initials: TL
authors.lastname: Doan
authors.forename: Gunda I
authors.initials: GI
authors.lastname: Georg
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D045786:Diterpenes, Kaurane / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009795:Octanes / Q000737:chemistry
chemical_list: D001688:Biological Products; D045786:Diterpenes, Kaurane; D005960:Glucosides; D009795:Octanes; C515747:isosteviol; C012043:stevioside; C012042:steviol; C026728:octane