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For other synthetic approaches to the spirocyclic pyrrolidinone portion of the oxazolomycins, see Ref. 18 and
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For other synthetic approaches to the spirocyclic pyrrolidinone portion of the oxazolomycins, see Ref. 18 and. Andrews M.D., Brewster A.G., and Moloney M.G. Synlett (1996) 612-614
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Note added in proof: after the submission of this paper a second synthesis of neooxazolomycin was reported ( )
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Note added in proof: after the submission of this paper a second synthesis of neooxazolomycin was reported (. Onyango E.O., Tsurumoto J., Imai N., Takahashi K., Ishihara J., and Hatakeyama S. Angew. Chem., Int. Ed. 46 (2007) 6703-6705 )
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For reviews see:
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For reviews see:
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42249083971
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These model studies were based on the following transformation:
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These model studies were based on the following transformation:
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51
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42249092377
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{A figure is presented}The R- and S- enantiomers of I were separated using HPLC with a Daicel Chiralcel OD column, eluting with 9:1 hexane-isopropanol. Variation of solvent, stoichiometry of reagents, times and temperatures gave ee's in the range 53-84% (with yields generally in the 80-90% range). The optimum ee was obtained using the l-valine-derived oxazaborolidinone 25a (84% ee) but the l-phenylalanine-derived oxazaborolidinone 25b was also effective giving I in 82% ee.
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{A figure is presented}The R- and S- enantiomers of I were separated using HPLC with a Daicel Chiralcel OD column, eluting with 9:1 hexane-isopropanol. Variation of solvent, stoichiometry of reagents, times and temperatures gave ee's in the range 53-84% (with yields generally in the 80-90% range). The optimum ee was obtained using the l-valine-derived oxazaborolidinone 25a (84% ee) but the l-phenylalanine-derived oxazaborolidinone 25b was also effective giving I in 82% ee.
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52
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0029979566
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Copper thiophene carboxylate-induced coupling ( ) was investigated to avoid the presence of palladium. However, this procedure gave triene 27 in only 20% yield with complete isomerisation
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Copper thiophene carboxylate-induced coupling (. Allred G.D., and Liebeskind L.S. J. Am. Chem. Soc. 118 (1996) 2748-2749 ) was investigated to avoid the presence of palladium. However, this procedure gave triene 27 in only 20% yield with complete isomerisation
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Allred, G.D.1
Liebeskind, L.S.2
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57
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42249099693
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A range of conditions were investigated for the direct conversion of ester I (R=Me) into the required primary amide II but without success. With acid I (R=H) a number of peptide coupling procedures were explored, the most promising of which utilised HATU in THF (83%), HBTU (69%) and EDCI·HCl/HOBt (29%).{A figure is presented}
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A range of conditions were investigated for the direct conversion of ester I (R=Me) into the required primary amide II but without success. With acid I (R=H) a number of peptide coupling procedures were explored, the most promising of which utilised HATU in THF (83%), HBTU (69%) and EDCI·HCl/HOBt (29%).{A figure is presented}
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61
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Franci X., Martina S.L.X., McGrady J.E., Webb M.R., Donald C., and Taylor R.J.K. Tetrahedron Lett. 44 (2003) 7735-7740
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62
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42249088934
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The ease with which aldehyde Z,Z-16 undergoes isomerisation meant that this modified approach could not be employed to prepare inthomycin A.
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The ease with which aldehyde Z,Z-16 undergoes isomerisation meant that this modified approach could not be employed to prepare inthomycin A.
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63
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0001115555
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Itsuno S., Watanabe K., Matsumoto T., Kuroda S., Yokoi A., and El-Shehawy A. J. Chem. Soc., Perkin Trans. 1 (1999) 2011-2016
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