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MICHAEL ADDUCTS OF LEVOGLUCOSENONE WITH α-ETHOXYCARBONYL- AND α-NITROCYCLODODECANONES: TRANSFORMATION INTO CHIRAL MACROLIDES

Лилия Х. Файзуллина, Юлия С. Галимова, Шамиль М. Салихов, Фарид А. Валеев
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Abstract


Levoglucosenone reacted with α-ethoxycarbonyl- and α-nitrocyclododecanones, leading to the formation of diastereomeric Michael adducts in high yields. Methods were developed for the denitration of the respective nitroadducts by treatment with Raney nickel and Bu3SnH, allowing to optimize the synthesis of a 16-membered chiral macrolide.

Keywords


levoglucosenone; macrolides; Michael adducts; ketalization.

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