- Synthesis of novel carbocyclic nucleoside analogues derived from 7-oxabicyclo[2.2.1]heptane-2-methanol
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Hydroboration of [(lR*,2R*,4R*)-7-oxabicyclo[2.2.1]hept- 5-en-2-yl]methyl benzoate (5), which was prepared by Diels-Alder reaction of furan with acrolein and subsequent reduction and benzoylation of the Diels-Alder product, afforded [(lR*,2S*,4S*,6S*)-6-h
- Hrebabecky, Hubert,Dracinsky, Martin,De Palma, Armando M.,Neyts, Johan,Holy, Antonin
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experimental part
p. 487 - 502
(2009/07/11)
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- Sulfone Directed Alkylative Bridge Cleavage of Oxabicyclic Vinyl Sulfones with Organolithium Reagents
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An efficient regio- and stereocontrolled methodology for the alkylative bridge cleavage of oxabicyclic vinyl sulfones is described.A range of 7-oxabicycloheptenyl and 8-oxabicyclooctenyl sulfones has been found to undergo an overall syn SN2' opening when treated with a wide variety of organolithium reagents and lithium aluminum hydride.In this manner, highly functionalized cyclohexenyl and cycloheptenyl sulfones, versatile synthetic intermediates, are now available in high yields.The complete stereoselectivity encountered in the exo conjugate addition may by explained by chelation of the organometallic reagent with the oxygen bridge and steric factors.Furthermore, less-strained substrates allow for complete control of the addition and elimination stages.
- Arjona, Odon,Dios, Alfonso de,Pradilla, Roberto Fernandez de la,Plumet, Joaquin,Viso, Alma
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p. 3906 - 3916
(2007/10/02)
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- Regioselective electrophilic additions to 2-alkoxy- and 2-alkoxymethyl-7-oxabicyclo[2.2.1]hept-5-ene derivatives
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The influence of the stereochemistry at C-2 on the selectivity of the reaction between PhSeBr and 2-alkoxymethyl substituted oxanorbornenes has been studied. All endo isomers displayed complete regio- and stereocontrol with incorporation of the electrophi
- Arjona,Fernandez De La Pradilla,Pita-Romero,Plumet,Viso
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p. 8199 - 8206
(2007/10/02)
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