Campus Units
Chemistry
Document Type
Article
Publication Version
Published Version
Publication Date
10-1987
Journal or Book Title
The Journal of Organic Chemistry
Volume
52
Issue
22
First Page
4841
Last Page
4846
DOI
10.1021/jo00231a003
Abstract
11-Deoxydaunomycinone (6), ita 4-deoxy analogue 5, and 1-methoxy-4,ll-dideoxyduanomycinone were prepared by a sequence involving an intramolecular acyl transfer reaction followed by a tandem Claisen-Diels-Alder reaction. The resulting diketone could be oxidized to naphthoquinone 11 with DDQ. This quinone was then treated with either 1-[ (trimethylsilyl)oxy]butadiene or l-methoxy-1,3-cyclohexadiene to provide adducts that could be transformed into 5 and 6. Unfortunately, the presence of the C-7 carbonyl group decreased the regioselectivity of 11 in Diels-Alder reactions.
Copyright Owner
American Chemical Society
Copyright Date
1987
Language
en
File Format
application/pdf
Recommended Citation
Kraus, George A. and Woo, Soon Hyung, "Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategy" (1987). Chemistry Publications. 677.
https://lib.dr.iastate.edu/chem_pubs/677
Included in
Environmental Chemistry Commons, Inorganic Chemistry Commons, Organic Chemistry Commons, Other Chemistry Commons, Polymer Chemistry Commons
Comments
Reprinted (adapted) with permission from The Journal of Organic Chemistry,52(22); 4841-4846. Doi: 10.1021/jo00231a003. Copyright 1987 American Chemical Society.