Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B.
The regioselectivities of several Diels-Alder reactions utilized en route to bisanthraquinone antibiotic BE-43472B are examined using density functional theory calculations. These reactions involve highly substituted dienes and juglone dienophiles, and there is an opposite regiochemical outcome for Diels-Alder reactions with beta-aryl substituted juglones when compared to reactions of unsubstituted juglone. In this article, the effect of an aromatic conjugating group bonded to juglone is explored.
Hayden
Amy E
AE
Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive, Los Angeles, California 90095-1569, USA.
Paton
Robert S
RS
Becker
Jochen
J
Lim
Yee Hwee
YH
Nicolaou
K C
KC
Houk
K N
KN
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D013237:Stereoisomerism
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; C540975:BE-43472B; D001688:Biological Products; D009285:Naphthoquinones; C005134:juglone