Origins of selectivity in pericyclic reaction cascades for the synthesis of gambogin and lateriflorone.
[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.
Hayden
Amy E
AE
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Xu
Hao
H
Nicolaou
K C
KC
Houk
K N
KN
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
D000475:Alkenes; D001952:Bridged-Ring Compounds; D011083:Polycyclic Compounds; D013141:Spiro Compounds; C511468:gambogin; C476169:lateriflorone