205934-63-0Relevant academic research and scientific papers
Studies on the synthesis of the C-glycosidic part of nogalamycin, part 2
Krohn, Karsten,Floerke, Ulrich,Keine, Juergen,Terstiege, Ina
, p. 171 - 195 (2007/10/03)
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.
