Michael Adducts of Levoglucosenone with α-Ethoxycarbonyl- and α-Nitrocyclododecanones: Transformation into Chiral Macrolides

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 synthes...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-11, Vol.56 (11), p.1434-1439
Main Authors: Faizullina, Liliya Kh, Galimova, Yulia S., Salikhov, Shamil M., Valeev, Farid A.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02834-x