title: Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone.
abstract: [reaction: see text] Quantum mechanical calculations demonstrate that the second step of a Claisen-Diels-Alder reaction cascade controls regioselectivity that gives advanced intermediates for the synthesis of gambogin and 1-O-methyllateriflorone.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
authors.forename: Amy E
authors.initials: AE
authors.lastname: Hayden
authors.forename: Hao
authors.initials: H
authors.lastname: Xu
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics
chemical_list: D000475:Alkenes; D001952:Bridged-Ring Compounds; D011083:Polycyclic Compounds; D013141:Spiro Compounds; C511468:gambogin; C476169:lateriflorone