Organic letters

Synthesis of spiroacetal enol ethers by oxidative activation of furan derivatives

J Robertson, S Naud

Index: Robertson, Jeremy; Naud, Sebastien Organic Letters, 2008 , vol. 10, # 23 p. 5445 - 5448

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Citation Number: 21

Abstract

Activation of furan by electron transfer combines with the radical stabilizing effect of the alkynyl substituent (R= Ph, MeC C−) to achieve site-selective cation formation. A tethered hydroxy group acts as a probe of this site-selectivity to produce the ring system present in spirocyclic natural products found in Artemisia and Chrysanthemum species. cis- Dihydroxylation proceeds with high anti-stereoselectivity with respect to the ...