title: DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085.
abstract: DFT calculations show that aromatic and bis-methoxy substituent effects in a synthetic precursor of TAN-1085 strongly favor a [1,7] sigmatropic hydrogen shift over the 6 pi electrocyclic pathway, rendering the latter unfavorable in synthesis.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
authors.forename: Zeve R
authors.initials: ZR
authors.lastname: Akerling
authors.forename: Joseph E
authors.initials: JE
authors.lastname: Norton
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D008958:Models, Molecular; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D009005:Monosaccharides; D011083:Polycyclic Compounds; C498261:TAN-1085