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Three-Component Coupling Approach to Trachyspic Acid

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journal contribution
posted on 2011-10-07, 00:00 authored by Daniel C. Schmitt, Leighann Lam, Jeffrey S. Johnson
Three-component coupling of the lithium enolate of t-BuOAc, silyl glyoxylate, and an α,β-unsaturated ketone enables the rapid construction of the trachyspic acid carbon skeleton. A 3,4-disubstituted isoxazole is utilized to mask the C7/C9 dicarbonyl. New enolsilane/nitrile-oxide cycloadditions enable the preparation of various 3,4-disubstituted isoxazoles that are challenging to access by other means.

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