- Abstract:
- 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.
- Publication status:
- Published
- Publisher copy:
- 10.1021/jo902572y
-
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- Journal:
- The Journal of organic chemistry
- Volume:
- 75
- Issue:
- 3
- Pages:
- 922-928
- Publication date:
- 2010-02-05
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
- URN:
-
uuid:eea7479e-3080-46c2-80c1-6f87956cc93c
- Source identifiers:
-
117666
- Local pid:
- pubs:117666
- Copyright date:
- 2010
Journal article
Origins of regioselectivity of Diels-Alder reactions for the synthesis of bisanthraquinone antibiotic BE-43472B.
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