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. 2020 Sep 30;11(40):10939–10944. doi: 10.1039/d0sc04686h

Scheme 4. Synthetic and NMR support for the structural reassignment of spiroviolene (4): (a) BH3·THF (1.0 equiv.), THF, 0 °C, 5 h, then NaOH/H2O2 (1 : 1), 23 °C, 1 h, 58%; (b) TCDI (3.0 equiv.), 4-DMAP (0.5 equiv.), CH2Cl2/pyridine (1 : 1), 23 °C, 12 h; (c) n-Bu3SnH (2.0 equiv.), AIBN (0.15 equiv.), toluene, 110 °C, 10 min, 47%; (d) 6 M HCl/THF (1 : 2), 50 °C, 4 h, >99%; (e) TCDI (4.0 equiv.), 4-DMAP (0.5 equiv.), CH2Cl2/pyridine (1 : 1), 23 °C, 12 h; (f) (TMS)3SiH (4.0 equiv.), AIBN (0.2 equiv.), toluene, 110 °C, 30 min.

Scheme 4