TY - JOUR
T1 - Structure assignment of aminoconduritols by 15N NMR correlation spectroscopy; synthesis of a positional isomer of 7-deoxypancratistatin
T2 - Canadian Journal of Chemistry
AU - Schilling, S.
AU - Rinner, U.
AU - Chan, C.
AU - Ghiviriga, I.
AU - Hudlicky, T.
N1 - Export Date: 13 June 2023; Cited By: 21; Correspondence Address: T. Hudlicky; Department of Chemistry, University of Florida, Gainesville, FL 32611, United States; email: [email protected]; CODEN: CJCHA
PY - 2001/11
Y1 - 2001/11
N2 - A positional isomer of 7-deoxypancratistatin was synthesized in 12 steps from epoxyaziridines 4 and 5. An intermolecular opening of the aziridine rather than the epoxide in the early stages of the synthesis led to 13, which did not match the properties of tetraacetate 10 derived from 7-deoxypancratistatin. At no stage of the synthesis did standard NMR techniques, involving 1H-1H or 1H-13C coupling, prove adequate for the structure assignment. Unambiguous structure was assigned by 1H-15N correlation NMR spectroscopy as well as by the conversion of epoxide 11 to diol 29 synthesized independently by another route. Experimental and spectral details are reported for all new compounds.
AB - A positional isomer of 7-deoxypancratistatin was synthesized in 12 steps from epoxyaziridines 4 and 5. An intermolecular opening of the aziridine rather than the epoxide in the early stages of the synthesis led to 13, which did not match the properties of tetraacetate 10 derived from 7-deoxypancratistatin. At no stage of the synthesis did standard NMR techniques, involving 1H-1H or 1H-13C coupling, prove adequate for the structure assignment. Unambiguous structure was assigned by 1H-15N correlation NMR spectroscopy as well as by the conversion of epoxide 11 to diol 29 synthesized independently by another route. Experimental and spectral details are reported for all new compounds.
KW - <sup>15</sup>N NMR spectroscopy
KW - Aminoconduritols
KW - Iso-7-deoxypancratistatin
KW - Lewis acid catalyzed intramolecuar opening of epoxides
KW - Nuclear magnetic resonance spectroscopy
KW - Synthesis (chemical)
KW - 2 acetylamino 1,3,4 triacetoxy 1,2,3,4,4a,11b hexahydro 1h 5,8,10 trioxacyclopenta[b]phenanthrene 6 one
KW - 5,6 (isopropylidenedioxy) 3 (4' methylphenylsulfonyl) 8 oxa 3 azatricyclo[5.1.0.0]octane
KW - 7 deoxypancreastatin
KW - acetic acid derivative
KW - aziridine derivative
KW - conduritol aziridine
KW - epoxide
KW - hexane
KW - ketone derivative
KW - octane
KW - pancreastatin
KW - unclassified drug
KW - [2 (benzo[1,3]dioxol 5 ylmethoxy) 3 [n benzyl(4' methylphenylsulfonyl)amino] 1,6 dihydroxy 4,5 (isopropylidenedioxy)]hexane
KW - Structure assignments
KW - article
KW - carbon nuclear magnetic resonance
KW - isomer
KW - nuclear magnetic resonance spectroscopy
KW - proton nuclear magnetic resonance
KW - synthesis
KW - Isomers
U2 - 10.1139/v01-139
DO - 10.1139/v01-139
M3 - Article
SN - 0008-4042
VL - 79
SP - 1659
EP - 1667
JO - Can. J. Chem.
JF - Can. J. Chem.
IS - 11
ER -