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The tert-butyl N-hydroxycarbamate-derived nitroso reagent 1 reacted with N-Cbz-protected spirocyclic diene 2 to provide spirocycloadduct 3. Here we describe the efficient conversion of 3 into the novel carbocyclic nucleoside spironoraristeromycin 4.

journal of organic chemistry

Diastereoselective Synthesis of a Spironoraristeromycin Using an Acylnitroso Diels−Alder Reaction<sup>†</sup>† We dedicate this paper to Prof. Jeremiah P. Freeman on the occasion of his 80th birthday and with deep gratitude for his 25 years of service to organic chemistry as secretary of<i>Organic Syntheses</i>.