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Article
Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategy
The Journal of Organic Chemistry
  • George A. Kraus, Iowa State University
  • Soon Hyung Woo, Iowa State University
Document Type
Article
Publication Version
Published Version
Publication Date
10-1-1987
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.
Comments

Reprinted (adapted) with permission from The Journal of Organic Chemistry,52(22); 4841-4846. Doi: 10.1021/jo00231a003. Copyright 1987 American Chemical Society.

Copyright Owner
American Chemical Society
Language
en
File Format
application/pdf
Citation Information
George A. Kraus and Soon Hyung Woo. "Total synthesis of 11-deoxydaunomycinone and analogs by a tandem Claisen-Diels-Alder strategy" The Journal of Organic Chemistry Vol. 52 Iss. 22 (1987) p. 4841 - 4846
Available at: http://works.bepress.com/george_kraus/215/