## 2 Materials and Methods
### Phenolic Nor-Triterpenes
#### Preparation of Compounds **7-9**  
A mixture of pristimerin (622.0 mg) and Pd/C 5% (100 mg) in acetic acid (15 mL) was stirred under 1 atmosphere of hydrogen for 3 h. The reaction mixture was filtered through a pad of celite, the solution quenched by addition of saturated aqueous sodium bicarbonate solution, and the aqueous residue extracted with dichloromethane (3 \(\times\) 30 mL). Then, to the crude, pyridine (1.5 mL) dissolved in acetic anhydride (1.5 mL) was added, and the reaction mixture was stirred for 12 h at room temperature. Upon completion of the reaction, the solution was concentrated on a cold finger with liquid nitrogen. The residue was purified by HPLC using _n_-hexane-ethyl acetate (8:2) as eluent to give compound **7** (21.9 mg, 2.9%, t\({}_{\rm R}\) = 11.4 min), reported elsewhere [31], and derivatives **8** (76.4 mg, 10.3%, t\({}_{\rm R}\) = 12.3 min) and **9** (32.1 mg, 4.3%, t\({}_{\rm R}\) = 12.6 min), not previously reported. 2,3-Diacetyllpristimerol (**7**). Pale yellow amorphous solid; [\(\alpha\)]\({}_{\rm D}^{20}\) - 15.5 (\(c\) 0.15, MeOH); UV (EtOH) \(\lambda_{\rm max}\) (log \(\varepsilon\)) 278 (7.3), 203 (7.4), 201 (7.3) nm; IR \(\
u_{\rm max}\) (film) 2927, 2870, 1775, 1729, 1649, 1371, 1214, 1188, 756 cm\({}^{-1}\); \({}^{1}\)H NMR (500 MHz, CDCl\({}_{3}\)) 8 0.58 (3H, s, Me-27), 1.08 (3H, s, Me-28), 1.17 (3H, s, Me-30), 1.22 (3H, s, Me-26), 1.35 (3H, s, Me-25), 2.06 (3H, s, Me-23), 2.28 (3H, s, OAc-2), 2.31 (3H, s, OAc-3), 3.06 (1H, d br, \(J\) = 15.7 Hz, H-6), 3.32 (1H, dd, \(J\) = 5.1, 15.7 Hz, H-6\(\alpha\)), 3.55 (3H, s, OMe-29), 5.73 (1H, d, \(J\) = 5.1 Hz, H-7), 7.00 (1H, s, H-1). \({}^{13}\)C NMR (100 MHz, CDCl\({}_{3}\)) 8 12.5 (q, C-23), 18.2 (q, C-27), 20.4 (q, OAc-2), 20.7 (q, OAc-3), 22.7 (q, C-26), 28.1 (t, C-6), 28.9 (t, C-15), 30.2 (t, C-12), 30.2 (t, C-19), 30.5 (t, C-22), 31.6 (q, C-28), 32.8 (q, C-30), 34.3 (q, C-25), 34.4 (t, C-11), 34.8 (s, C-17), 34.8 (t, C-21), 36.8 (t, C-16), 37.2 (s, C-13), 37.5 (s, C-9), 40.4 (s, C-20), 43.7 (s, C-14), 44.4 (d, C-18), 51.5 (q, OMe-29), 116.7 (d, C-1), 116.9 (d,C-7), 127.8 (s, C-4), 131.5 (s, C-5), 138.0 (s, C-3), 140.6 (s, C-2), 147.5 (s, C-10), 149.0 (s, C-8), 168.4 (s, OAc-2), 168.7 (s, OAc-3), 178.9 (s, C-29); EI-MS _n_/\(\underline{z}\) (%): 550 [M\({}^{+}\)] (1), 535 (8), 475 (16), 322 (7), 229 (17), 149 (9), 57 (100); EI-HRMS _m_/\(\underline{z}\) 550.3167 (calcaled. for C\({}_{34}\)H\({}_{46}\)O\({}_{6}\), 550.3192). 2,3-Diacetyl-6-deoxyblepharodol (8). Pale yellow amorphous solid; [\(\alpha\)]\({}_{\rm D}^{20}-29.5\) (\(c\) 0.20, MeOH); UV (EtOH) _\(\lambda\)max_ (log \(\varepsilon\)) 278 (7.3), 203 (7.3), 201 (7.2) nm; IR _vmax_ (film) 2937, 1773, 1730, 1462, 1371, 1213, 1040, 756 cm\({}^{-1}\); \({}^{1}\)H NMR (500 MHz, CDCl\({}_{3}\)) 8 0.78 (3H, s, Me-27), 0.88 (3H, s, Me-26), 1.10 (3H, s, Me-28), 1.60 (6H, s, Me-25, Me-30), 1.98 (3H, s, Me-23), 2.26 (3H, s, OAc-3), 2.30 (3H, s, OAc-2), 2.59 (1H, dd, \(J\) = 11.8, 15.7 Hz, H-6\(\alpha\)), 2.60 (1H, dd, \(J\) = 6.1, 15.7 Hz, H-6\(\alpha\)), 3.59 (3H, s, OMe), 6.89 (1H, s, H-1), 13C NMR (100 MHz, CDCl\({}_{3}\)) 8 12.5 (q, C-23), 15.9 (q, C-26), 17.3 (q, C-27), 18.2 (t, C-7), 20.4 (q, OAc-3), 20.6 (q, OAc-2), 27.3 (q, C-25), 28.6 (t, C-6), 28.9 (t, C-21), 30.0 (t, C-12), 30.1 (s, C-17), 30.2 (t, C-19), 30.5 (t, C-15), 31.8 (q, C-28), 31.9 (q, C-30), 33.8 (t, C-11), 36.2 (t, C-22), 36.5 (t, C-16), 37.2 (s, C-9), 38.9 (s, C-13), 39.4 (s, C-14), 40.5 (s, C-20), 43.5 (d, C-8), 44.5 (d, C-18), 51.5 (q, OMe-29), 116.2 (d, C-1), 129.4 (s, C-4), 132.7 (s, C-5), 138.0 (s, C-3), 139.9 (s, C-2), 149.7 (s, C-10), 168.4 (s, OAc-3), 168.8 (s, OAc-2), 179.1 (s, C-29); EI-MS _m_/\(\underline{z}\) (%) 552 [M\({}^{+}\)] (10), 510 (49), 495 (5), 468 (100), 453 (15), 249 (26), 190 (9); EI-HRMS _m_/\(\underline{z}\) 552.3457 (caled. for C\({}_{34}\)H\({}_{48}\)O\({}_{6}\), 552.3451). 2,3-Diacetyl-8-_epi_-6-deoxyblepharodol (9).