Figure 7: Formal total synthesis of the cortistatins. | Nature Communications

Figure 7: Formal total synthesis of the cortistatins.

From: Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction

Figure 7

(a) 2,2-Dimethylpropane-1,3-diol, Pyridinium p-Toluenesulfonate (PPTS) benzene, 50 °C, 4 h, 80%; (b) KH, MeI, THF, 0 °C to room temperature (rt), 92%; (c) CAN, borate buffer (pH=8.0), 60 °C, 5 h, 55%; (d) ethynylmagnesium chloride, THF, 0 °C to rt, 75%+20% diastereomer; (e) NBS, AgNO3, acetone, rt, 0.5 h, 90%; (f) Ph3PAuNTf2 (2.5 mol%), DCM, rt, 1 h, 81%; (g) allyl(Bu)3Sn, azodiisobutyronitrile (AIBN) benzene, 80 °C, 18 h, 78%; (h) PdCl2, CuCl, O2, DMF-H2O (7:1), rt, 12 h, 90%; (i) NaOMe, MeOH, rt, 10 h, 70%. (j) TMSOTf, Et3N, THF, 0 °C, 0.5 h, then NBS, THF, 0 °C, 1 h, 80%.

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