Synthesis of spiroacetal enol ethers by oxidative activation of furan derivatives.
Org Lett
; 10(23): 5445-8, 2008 Dec 04.
Article
em En
| MEDLINE
| ID: mdl-18986155
ABSTRACT
Activation of furan by electron transfer combines with the radical stabilizing effect of the alkynyl substituent (R = Ph, MeC[triple bond]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 tetrahydropyranyl ring oxygen.
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MEDLINE
Idioma:
En
Ano de publicação:
2008
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Article