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manuscript submitted
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The synthesis of the side chain 2 is disclosed in a separate publication: Miller, R. A.; Humphrey, G. R.; Lieberman, D. R.; Ceglia, S. S.; Grabowski, E. J. J. J. Org. Chem., manuscript submitted.
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note
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(c) We have realized an alternative, much simpler approach from the acid 9 to the hydroxymethyl ketone β-10: activation of 9 using carbonyldiimidazole is followed by reaction with the glycolic acid enolate. Acid workup with concomitant decarboxylation gives β-10 in 72% isolated yield.
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0343635329
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note
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Heptane was chosen for its commercial availability; running the reaction in nonane or in heptane under pressure at 120 °C allows completion of the reaction in 3 h.
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21
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0026493892
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0342765111
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3As.
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