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12
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0010233162
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note
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3) 161.4, 160.6 (2C), 142.5, 138.4, 138.1, 137.8, 135.6, 135.3, 118.6, 117.6, 88.8, 82.0, 77.4, 77.3, 39.3, 36.5, 34.8, 28.2, 25.8, 18.1, 14.3, 13.9, 13.8, 5.9, -4.1, -4.8.
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14
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0024816607
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15
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0028604352
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19
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0010241417
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note
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10. Treatment of 9a with TBSOTf afforded the undesired tetrahydropyran product 17 even at -78 °C, via a Lewis acid-promoted cyclisation with precedent in other work performed in this laboratory: (Equation Presented)
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-
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20
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0010243008
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note
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11. For R = Me, the minor regioisomer could not be removed until cyclisation to afford tetrahydropyran ester 12.
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22
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0000476716
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24
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0030876792
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0030852861
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1542421110
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29
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0010266271
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note
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15. Unfortunately, self-condensation of the aldehyde could not be avoided during equilibration with Triton-B methoxide, leading to a modest 52% recovery of configurationally pure 4.
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30
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0030792962
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0026101186
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32
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0010266272
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note
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17. The high (E)-selectivity is largely attributable to the use of the phosphonium ylid instead of the phosphonate, with the change of solvent from THF to DMF having little effect.
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