DFT study of pericyclic reaction cascades in the synthesis of antibiotic TAN-1085.
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.
Akerling
Zeve R
ZR
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Norton
Joseph E
JE
Houk
K N
KN
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
D000900:Anti-Bacterial Agents; D009005:Monosaccharides; D011083:Polycyclic Compounds; C498261:TAN-1085