Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B.

Journal article

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.

Authors: Hayden, A; Paton, R; Becker, J; Lim, Y; Nicolaou, K

• Publication status: Published
• Journal: Journal of organic chemistry
• Volume: 75
• Issue: 3
• Pages: 922-928
• Publication date: 2010-02-01
• DOI: 10.1021/jo902572y
• EISSN: 1520-6904
• ISSN: 0022-3263
• Language: English
• Keywords: Biological Products; Crystallography, X-Ray; Naphthoquinones; Molecular Conformation; Molecular Structure; Stereoisomerism; Anthraquinones; Anti-Bacterial Agents