Studies on the synthesis of the C-glycosidic part of nogalamycin, part 2

Article abstract of DOI:10.1080/07328309808002321

The stereochemistry of the addition of metalloaryls 11w-z to the methyl ketones 10a-e was studied in connection with the construction of the nogalamycin C-glycoside. Excellent selectivities towards the (S)-isomer 13a were observed in the β-chelate model B in the reaction of the benzyl ethers 10a with the cerium reagent 11y and the titanium reagent 11z or the alcohol 10c with the lithium compound 11w. A moderate 3:1 selectivity in favor of the desired (R)-isomer was observed in the reaction of the silyl ether 10d with 11w. A reversal of the addition sequence (reaction of 15a with MeMgI) led exclusively to 13a whereas the alcohol 15c gave a 5:3 mixture of 12c:13c.

Full text of DOI:10.1080/07328309808002321

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Journal of Carbohydrate Chemistry
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Studies on the Synthesis of the C-
Glycosidic Part of Nogalamycin, Part 2
Karsten Krohn a , Ulrich Flörke a , Jürgen Keine a & Ina Terstiege a
a Fachbereich Chemie und Chemietechnik , Universität-GH
Paderborn , Warburger Str. 100, D-33098, Paderborn, Germany E-
mail:
Published online: 16 Aug 2006.
To cite this article: Karsten Krohn , Ulrich Flörke , Jürgen Keine & Ina Terstiege (1998) Studies on the
Synthesis of the C-Glycosidic Part of Nogalamycin, Part 2, Journal of Carbohydrate Chemistry, 17:2,
171-195
To link to this article: http://dx.doi.org/10.1080/07328309808002321
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