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. 2020 Apr 23;25(8):1970. doi: 10.3390/molecules25081970

Table 1.

Optimization of oxidative lactonization conditions.

graphic file with name molecules-25-01970-i001.jpg

Entry Condition (Equivalent) Result
1
  • (i)

    OsO4 (0.02), NMO (4.0) in acetone/water

  • (ii)

    NaIO4 (2.0) in THF/water

  • (iii)

    NaOAc (2.0), PCC (2.0) in CH2Cl2

 71% (3 steps)
2
  • (i)

    OsO4 (0.01), NaIO4 (4.0) in dioxane/water

  • (ii)

    NaOAc (2.0), PCC (4.0) in CH2Cl2

 51% (2 steps)
3
  • (i)

    OsO4 (0.01), NaIO4 (4.0), pyridine (2.0) in dioxane/water

  • (ii)

    NaOAc (2.0), PCC (4.0) in CH2Cl2

 64% (2 steps)
4
  • (i)

    OsO4 (0.01), NaIO4 (4.0), 2,6-lutidine (2.0) in dioxane/water

  • (ii)

    NaOAc (2.0), PCC (2.0) in CH2Cl2

 73% (2 steps)
5 OsO4(0.01), Oxone® (4.0) in DMF N.R. a (1 step)

a No reaction. The bold is lactonization condition after optimization.