Rearrangement of isoxazoline-5-spiro derivatives. Part 10. Regioselective nitrone cycloadditions to MethoxycarbonylMethylenecyclopropane (cas 110793-87-8): Synthesis of precursors of (±)-Lupinine, (±)-Epilupinine and (±)-Elaeokanine A☆

Add time:08/17/2019    Source:sciencedirect.com

The cycloaddition of cyclic nitrones to methoxycarbonylmethylenecyclopropane (1) gives adducts having the methoxycarbonyl group on C-4 of the isoxazolidine ring with high regioselectivity. The thermal rearrangement of the adducts gives quinolizidinone 6 and indolizidinones 8 bearing the methoxycarbonyl group selectively at C-1 and at C-8, respectively. The two compounds are intermediates for new formal syntheses of the alkaloids (±)-Lupinine and (±)-Epilupinine, and (±)-Elaeokanine A, respectively.

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