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. 2021 Jul 19;64(15):11496–11526. doi: 10.1021/acs.jmedchem.1c00806

Scheme 6. General Preparation of 14, 16–18, 28, and 29.

Scheme 6

Reagents and conditions: (a) TosCl, Et3N, DCM, rt., 4 h, 60%; (b) for 58–60 methyl acrylate Grubbs-II catalyst, CDCl3, reflux, 3 days, 10% for 58, 30% for 59, 49% for 60; (c) for 61 methyl methacrylate Hoveyda–Grubbs-II catalyst, CDCl3, MW 120 °C, 2.5 h, 21%; (d) LiOH, THF/MeOH/H2O (3:1:1), 40 °C, 16 h; (e) KOH, MeOH, reflux, 6 h, 16% for 14, 31% for 16, 17% for 17, 20% for 18, 53% for 28, 57% for 29; (f) 2-methylene-1,3-propanediacetate, Grubbs-II catalyst, CDCl3, MW 120 °C, 2 h, 27% for 62, 38% for 63.