

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

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.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv