Studies on the synthesis of the C-glycosidic part of nogalamycin, part 1

Article abstract of DOI:10.1080/07328309808002320

Studies aimed at the construction of the C-glycosidic part of nogalamycin (1) and menogarol (2) are described. The stereochemistry of the addition of aryl lithiums to 4-acetyl-1,3-dioxolane 16, prepared from D-glucose via 10a-15, was studied. The major isomers were the (S)-isomers 17a and 17b as shown by X-ray analysis of 17a with the unnatural configuration. The adduct 17a was further converted to the anomeric naphthoquinones 22a and 22b by acetal cleavage, ozonolysis, acetalization and Diels-Alder reaction with 1-methoxybutadiene.

Full text of DOI:10.1080/07328309808002320

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Journal of Carbohydrate Chemistry
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Studies on the Synthesis of the C-
Glycosidic Part of Nogalamycin, Part 1
Karsten Krohn a , Vadiraj S. Ekkundi a , Detlev Döring a & Peter Jones
b
a Fachbereich Chemie und Chemietechnik , Universität-GH
Paderborn , Warburger Str. 100, D-33098, Paderborn, Germany E-
mail:
b Institut für Anorganische Chemie , TU Braunschweig, Hagenring 30,
D-38106, Braunschweig, Germany
Published online: 16 Aug 2006.
To cite this article: Karsten Krohn , Vadiraj S. Ekkundi , Detlev Döring & Peter Jones (1998) Studies
on the Synthesis of the C-Glycosidic Part of Nogalamycin, Part 1, Journal of Carbohydrate Chemistry,
17:2, 153-170, DOI: 10.1080/07328309808002320
To link to this article: http://dx.doi.org/10.1080/07328309808002320
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