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Synthesis 1995; 1995(12): 1493-1495
DOI: 10.1055/s-1995-4136
short paper
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6-Oxoestradiols from Estradiols: Exploiting Site Selective Metalation of Aralkyl Systems with Superbases

Rosanna Tedesco, Rita Fiaschi, Elio Napolitano*
  • *Università di Pisa, Dipartimento di Chimica Bioorganica, Via Bonanno 33, I-56126 Pisa, Italy, Fax +39(50)43321; Scuola Normale Superiore, Piazza dei Cavalieri, I-56100 Pisa, Italy
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Publikationsdatum:
31. Dezember 2000 (online)

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3-O-Protected estradiol derivatives undergo metalation at C-6 when exposed to a fourfold excess of the reagent consisting of an equimolar mixture of lithium diisopropylamide and potassium 1,1-dimethylpropoxide (3 h, THF, -78°C). The metalated intermediates can be oxidized by quenching with trimethyl borate followed by treatment with hydrogen peroxide, thus allowing the introduction of a 6-hydroxy group into the estradiol framework. Further oxidation of the 6-hydroxy group gives O-protected 6-oxoestradiols.

superbases - benzyl deprotonation - hydrogen-metal exchange - estradiol - hydroxylation