Journal article icon

Journal article

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

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

Actions


Access Document


Publisher copy:
10.1021/jo902572y

Authors


Hayden, AE More by this author
Nicolaou, KC More by this author
Expand authors...
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

Terms of use


Metrics



If you are the owner of this record, you can report an update to it here: Report update to this record

TO TOP