Intramolecular Oxonium Ylide Formation–[2,3] Sigmatropic Rearrangement of Diazocarbonyl-Substituted Cyclic Unsaturated Acetals: A Formal Synthesis of Hyperolactone C

Rh­(II)-catalyzed oxonium ylide formation–[2,3] sigmatropic rearrangement of α-diazo-β-ketoesters possessing γ-cyclic unsaturated acetal substitution, followed by acid-catalyzed elimination–lactonization, provides a concise approach to 1,7-dioxaspiro­[4.4]­non-2-ene-4,6-diones. The process creates a...

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Veröffentlicht in:	Journal of organic chemistry 2014-10, Vol.79 (20), p.9728-9734
Hauptverfasser:	Hodgson, David M, Man, Stanislav, Powell, Kimberley J, Perko, Ziga, Zeng, Minxiang, Moreno-Clavijo, Elena, Thompson, Amber L, Moore, Michael D
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetals - chemistry Furans - chemical synthesis Furans - chemistry Molecular Structure Onium Compounds - chemistry Rhodium - chemistry Spiro Compounds - chemistry Stereoisomerism
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