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33748774444
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9
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84924243818
-
-
The reaction was completed in 12 days, reduced to 5 days when the reaction temperature was increased by using propionic anhydride; however, the yield dropped to ca. 25%
-
(a) The reaction was completed in 12 days, reduced to 5 days when the reaction temperature was increased by using propionic anhydride; however, the yield dropped to ca. 25%.
-
-
-
-
10
-
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84924237566
-
-
The isolation and purification of 9 turned out to be tedious
-
(b) The isolation and purification of 9 turned out to be tedious.
-
-
-
-
11
-
-
84924255203
-
-
note
-
Compound 12 was obtained in only 36% yield even after reflux for 4 days, along with the recovery of 45% of the starting material 11. Similar results were observed when acetone was used as the solvent. When alcohols were used as solvent, only the debenzylation product (i.e., compound 10) could be detected. For example, a quantitative amount of 10 was obtained when 11 was treated with BnBr in 4-methyl-2-pentanol (bp 131-134 °C) under reflux for 4 h.
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12
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56349168456
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84924244483
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For examples, see: (a) Reference 11b
-
For examples, see: (a) Reference 11b.
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4544289291
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33750681286
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0035850522
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0000813254
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30
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84924277748
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The stoichiometries of PEMgCl and additives, as listed in Table 1, were adjusted to ensure the completion of the reactions, but were not fully optimized
-
The stoichiometries of PEMgCl and additives, as listed in Table 1, were adjusted to ensure the completion of the reactions, but were not fully optimized.
-
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-
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33
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0033972449
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33847015647
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33845280557
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0038753596
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37
-
-
84924280416
-
-
As measured by HPLC, after DIBAL-H reduction to a mixture of hydroxyl compounds (i.e., 25 and 26)
-
As measured by HPLC, after DIBAL-H reduction to a mixture of hydroxyl compounds (i.e., 25 and 26).
-
-
-
-
38
-
-
84924279602
-
-
The stereochemistry at C-4 of 25 and 26 was confirmed by NOESY experiments of their corresponding cyclization products 2 and 3
-
The stereochemistry at C-4 of 25 and 26 was confirmed by NOESY experiments of their corresponding cyclization products 2 and 3.
-
-
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