136969-15-8Relevant academic research and scientific papers
Sequential 1,3-dipolar cycloadditions in the synthesis of bis-isoxazolo substituted piperidinones
Huang, Kevin Sheng-Lin,Lee, Edwin H.,Olmstead, Marilyn M.,Kurth, Mark J.
, p. 499 - 503 (2000)
A strategy for the efficient synthesis of novel bis-isoxazolo substituted piperidinones has been developed. The protocol consists of the Michael addition of an unsaturated alkoxide to β-nitrostyrene followed by an intramolecular nitrile oxide cycloaddition (INOC) or an intramolecular silyl nitronate olefin cycloaddition (ISOC) to give III. Grignard addition to this isoxazoline intermediate followed by DCC coupling of the resulting isoxazolidine with nitroacetic acid gave II, and a second intramolecular cycloaddition via 1,3-dipoles result in the formation of the targeted novel tetracycles (I). A solid-supported scavenger was employed to increase the efficiency and yield of the Michael addition step.
