title: Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Aminobicyclo[5.1.0]octitols.
abstract: A series of eight stereoisomeric N-(tetrahydroxy bicyclo-[5.1.0]oct-2S*-yl)phthalimides were prepared in one to four steps from N-(bicyclo[5.1.0]octa-3,5-dien-2-yl)phthalimide (±)-7, which is readily available from cyclooctatetraene (62 % yield). The structural assignments of the stereoisomers were established by (1) H NMR spectral data as well as X-ray crystal structures for certain members. The outcomes of several epoxydiol hydrolyses, particularly ring contraction and enlargement, are of note. The isomeric phthalimides as well as the free amines did not exhibit β-glucosidase inhibitory activity at a concentration of less than 100 μM.
authors.affiliation: Department of Chemistry, Marquette University, P. O. Box 1881 Marquette University, Milwaukee, WI 53201-1881 (USA).
authors.forename: Mohamed F
authors.initials: MF
authors.lastname: El-Mansy
authors.affiliation: Department of Chemistry, Marquette University, P. O. Box 1881 Marquette University, Milwaukee, WI 53201-1881 (USA).
authors.forename: Matthew
authors.initials: M
authors.lastname: Flister
authors.affiliation: Department of Chemistry, Marquette University, P. O. Box 1881 Marquette University, Milwaukee, WI 53201-1881 (USA).
authors.forename: Sergey
authors.initials: S
authors.lastname: Lindeman
authors.affiliation: School of Pharmacy, Concordia University Wisconsin, Mequon, WI 53097 (USA).
authors.forename: Kelsey
authors.initials: K
authors.lastname: Kalous
authors.affiliation: School of Pharmacy, Concordia University Wisconsin, Mequon, WI 53097 (USA).
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Sem
authors.affiliation: Department of Chemistry, Marquette University, P. O. Box 1881 Marquette University, Milwaukee, WI 53201-1881 (USA). William.donaldson@marquette.edu.
authors.forename: William A
authors.initials: WA
authors.lastname: Donaldson
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010797:Phthalimides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors
chemical_list: D000588:Amines; D001643:Bridged Bicyclo Compounds; D010797:Phthalimides; D013402:Sugar Alcohols; C037431:phthalimide; D001616:beta-Galactosidase
keywords: cyclitols; diastereoselectivity; epoxides; hydrocarbons; hydrolysis