MICHAEL ADDUCTS OF LEVOGLUCOSENONE WITH α-ETHOXYCARBONYL- AND α-NITROCYCLODODECANONES: TRANSFORMATION INTO CHIRAL MACROLIDES
Authors
Лилия Х. Файзуллина
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry,
Siberian Branch of the Russian Academy of Sciences,
9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
Юлия С. Галимова
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry,
Siberian Branch of the Russian Academy of Sciences,
9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
Шамиль М. Салихов
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry,
Siberian Branch of the Russian Academy of Sciences,
9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
Фарид А. Валеев
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry,
Siberian Branch of the Russian Academy of Sciences,
9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
levoglucosenone, macrolides, Michael adducts, ketalization.
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.
Author Biography
Лилия Х. Файзуллина, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry,
Siberian Branch of the Russian Academy of Sciences,
9 Akademika Lavrentieva Ave., Novosibirsk 630090, Russia
к.х.н. по специальности 02.00.03 органическая химия, доцент, старший научный сотрудник лаборатории фармакофорных циклических систем
