Table 1.
Evaluation of mupirocin methyl ester (14) cyclization leading to 15 and 16 with achiral catalysts and promoters.
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|---|---|---|---|---|---|
| Entry | Catalyst/conditions | Solvent | Time | Conversion [%] | 15/16[b] |
| 1[a] | LiCl | CH2Cl2 | 12 h | < 5 | - |
| 2[a] | ZnCl2 | CH2Cl2 | 12 h | 82 | 48:52 |
| 3[c] | Sc(OTf)3 | CH2Cl2 | 12 h | 77 | 57:43 |
| 4[d] | - | H2O | 4 d | 24 | 71:29 |
| 5 | KH2PO4 buffer (pH 7) | H2O | 4 d | > 98 | 48:52 |
| 6[e] | Cs2CO3 | CH3OH | 4 d | - | - |
| 7[f] | LiHMDS | THF | 4 d | - | - |
| 8[g] | (p-NO2-C6H4O)2PO2H | CH2Cl2 | 5 d | > 98 | 70:30 |
Conditions: 14 (0.02 mmol), catalyst (20 mol%), CH2Cl2 (0.01 m).
Determined by RP HPLC.
Conditions: catalyst (20 mol%), CH2Cl2 (0.2 m).
70°C.
Cs2CO3 (10 equiv), CH2Cl2 (0.02 m).
LiHMDS (3equiv), CH2Cl2 (0.01 m).
Catalyst (20 mol%), CH2Cl2 (0.2 m).
