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. Author manuscript; available in PMC: 2021 Apr 6.
Published in final edited form as: Chemistry. 2020 Mar 18;26(20):4583–4591. doi: 10.1002/chem.201905222

Table 1.

Evaluation of mupirocin methyl ester (14) cyclization leading to 15 and 16 with achiral catalysts and promoters.

graphic file with name nihms-1592116-t0007.jpg
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
[a]

Conditions: 14 (0.02 mmol), catalyst (20 mol%), CH2Cl2 (0.01 m).

[b]

Determined by RP HPLC.

[c]

Conditions: catalyst (20 mol%), CH2Cl2 (0.2 m).

[d]

70°C.

[e]

Cs2CO3 (10 equiv), CH2Cl2 (0.02 m).

[f]

LiHMDS (3equiv), CH2Cl2 (0.01 m).

[g]

Catalyst (20 mol%), CH2Cl2 (0.2 m).