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1 Supporting Information Wiley-VCH Weinheim, Germany

2 Concise Stereoselective Synthesis of ( )-Podophyllotoxin by Intermolecular Fe III -catalyzed Friedel-Crafts Alkylation Daniel Stadler, Thorsten Bach* Preparation Procedures, Analytical Data of Key Intermediates and Spectra of ( )-Podophyllotoxin Alcohol 5 H H Me Me Me Me Me Me C 16 H g/mol erythro-5 threo-5 Diisopropylamine (303 µl, 217 mg, 2.14 mmol, 1.20 eq.) was dissolved in 10 ml dry THF and cooled to 0 C. After addition of butyl lithium (785 µl, 1.96 mmol, 1.10 eq., 2.5 M solution in hexane) and stirring for 15 minutes, the mixture was cooled to 78 C and Taniguchi-lactone (3) (200 mg, 1.78 mmol, 1.00 eq.) was added. The solution was stirred for another 30 minutes. 3,4,5-Trimethoxybenzaldehyde (4, 385 mg, 1.96 mmol, 1.10 eq., dissolved in 5 ml THF) was added dropwise maintaining the low temperature. After another 3 hours, the reaction was quenched at 78 C by the rapid addition of saturated aqueous NH 4 Cl (20 ml) and allowed to warm to room temperature. The separated aqueous layer was extracted with Et 2 (2 20 ml). The combined organic layers were washed with saturated aqueous NaHC 3 (10 ml) and saturated aqueous NaCl (10 ml), dried over Na 2 S 4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (3 15 cm, P:Et 2 = 1:9 Et 2 ) to give 5 (518 mg, 1.68 mmol, 94%) in a diastereomeric mixture of erythro:threo = 52:48 (for analytical purposes, both compounds can be separated by flash chromatography). R f : 0.30 (erythro) / 0.23 (threo) (P:Et 2 = 1:9). [α] D 20 : erythro: 3.3 (c = 1.9, CH 2 Cl 2 ); threo: (c = 1.3, CH 2 Cl 2 ).

3 IR: (ATR), ~ v = 3433 cm 1 (br), 2943 (m), 2899 (w), 1752 (s), 1594 (s), 1462 (s), 1421 (s), 1120 (vs), 1010 (s). MS: (EI, 70 ev): m/z (%) = 308 (35), 290 (3), 197 (100), 169 (45), 154 (16), 138 (19). erythro-5: 1 H-NMR: (360 MHz, CDCl 3 ): δ [ppm] = 2.80 (dd, 3 J = 9.7 Hz, 3 J = 3.3 Hz, 1 H), 3.12 (br s, 1 H), (m, 1 H), 3.81 (s, 3 H), 3.83 (s, 6 H), 3.90 (virt. t, J 9.0 Hz, 1 H), 4.37 (virt. t, J 8.7 Hz, 1 H), 4.86 (d virt. t, 3 J = 17.0 Hz, J 1.1 Hz, 1 H), 4.89 (d virt. t, 3 J = 10.3 Hz, J 1.1 Hz, 1 H), 5.27 (d, 3 J = 3.3 Hz, 1 H), 5.40 (ddd, 3 J = 17.0 Hz, 3 J = 10.3 Hz, 3 J = 7.9 Hz, 1 H), 6.57 (s, 2 H). 13 C-NMR: (90.6 MHz, CDCl 3 ): δ [ppm] = 39.6, 52.8, 56.1, 60.9, 70.7, 71.0, 102.8, 117.4, 135.6, 136.3, 137.5, 153.3, threo-5: 1 H-NMR: (360 MHz, CDCl 3 ): δ [ppm] = 2.74 (dd, 3 J = 10.7 Hz, 3 J = 7.3 Hz, 1 H), (m, 1 H), 3.15 (br s, 1 H), 3.80 (s, 3 H), 3.83 (s, 6 H), 3.87 (virt. t, J 9.4 Hz, 1 H), 4.27 (dd, 3 J = 9.1 Hz, 3 J = 8.3 Hz, 1 H), 4.79 (d virt. t, 3 J = 17.1 Hz, J 1.0 Hz, 1 H), 4.83 (d virt. t, 3 J = 10.3 Hz, J 1.0 Hz, 1 H), 4.81 (d, 3 J = 7.3 Hz, 1 H), 5.30 (ddd, 3 J = 17.1 Hz, 3 J = 10.3 Hz, 3 J = 7.9 Hz, 1 H), 6.58 (s, 2 H). 13 C-NMR: (90.6 MHz, CDCl 3 ): δ [ppm] = 42.7, 52.0, 56.1, 60.8, 70.4, 74.2, 103.9, 117.6, 134.3, 135.4, 138.1, 153.3, CHN: calcd: C: H: 6.54; found: C: H: Phenol 6d: H C 23 H g/mol Me Me Me Cation precursor 5 (326 mg, 1.06 mmol, 1.00 eq.) and sesamol (2d, 584 mg, 4.23 mmol, 4.00 eq.) were dissolved in 20 ml dry CH 2 Cl 2 and FeCl 3 (8.6 mg, 52.9 µmol, 5 mol-%) was added. The solution was stirred at room temperature for 20 minutes. The reaction was quenched by the addition of saturated aqueous NaHC 3 (10 ml). The separated aqueous layer was extracted with Et 2 (2 10 ml). The combined organic layers were washed with saturated aqueous NaCl (10 ml), dried over Na 2 S 4, filtered

4 and concentrated under reduced pressure. The crude product was purified by flash chromatography (2 15 cm, P:Et 2 = 1:9) to give 6d (448 mg, 1.05 mmol, 99%) in a diastereomeric mixture of 96:4 (the diastereoisomers are not separable by flash chromatography, see next step for separation). R f : 0.29 (P:Et 2 = 1:9). [α] 20 D : (c = 1.8, CH 2 Cl 2 ). IR: (KBr), v ~ = 3374 cm 1 (br), 2938 (m), 2899 (w), 1755 (s), 1591 (s), 1506 (s), 1439 (s), 1173 (vs), 1122 (vs), 1035 (s). MS: (EI, 70 ev): m/z (%) = 428 (35), 317 (100), 285 (10), 168 (14). 1 H-NMR: (360 MHz, CDCl 3 ): δ [ppm] = (m, 1 H), 3.17 (virt. t, J 6.7 Hz, 1 H), 3.80 (s, 6 H), 3.82 (s, 3 H), 4.00 (dd, 2 J = 9.2 Hz, 3 J = 5.9 Hz, 1 H), 4.22 (dd, 2 J = 9.2 Hz, 3 J = 7.3 Hz, 1 H), 4.70 (d, 3 J = 6.9 Hz, 1 H), (m, 2 H), 5.55 (br s, 1 H), 5.80 (ddd, 3 J = 17.0 Hz, 3 J = 10.2 Hz, 3 J = 8.3 Hz, 1 H), 5.86 (d, 2 J = 1.5 Hz, 1 H), 5.87 (d, 2 J = 1.5 Hz, 1 H), 6.36 (s, 1 H), 6.52 (s, 2 H), 6.69 (s, 1 H). 13 C-NMR: (90.6 MHz, CDCl 3 ): δ [ppm] = 44.0, 44.3, 49.6, 56.2, 60.8, 70.7, 98.9, 101.1, 105.6, 108.6, 117.6, 119.5, 136.3, 136.6, 137.0, 141.4, 146.8, 148.2, 153.3, HRMS: (EI): calcd for C 23 H 24 8 [M + ]: ; found: Triflate 6c: Tf C 24 H 23 F 3 10 S g/mol Me Me Me Phenol 6d (382 mg, 892 µmol, 1.00 eq.) was dissolved in 20 ml dry CH 2 Cl 2 and cooled to 10 C. After addition of NEt 3 (247 µl, 180 mg, 1.78 mmol, 2.00 eq.) and Tf 2 (222 µl, 377 mg, 1.34 mmol, 1.50 eq.), the mixture was stirred for 25 minutes at this temperature. The reaction was quenched by addition of saturated aqueous NaHC 3 (10 ml). The separated aqueous layer was extracted with Et 2 (2 10 ml). The combined organic layers were washed with 2 N HCl (10 ml) and saturated aqueous NaCl (10 ml), dried over Na 2 S 4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (2 15 cm, P:Et 2 = 2:8) to give 6c (444 mg, 792 µmol, 89%) as a single diastereoisomer (the minor diastereoisomer generated in the former reaction can be separated at this stage).

5 R f : 0.40 (P:Et 2 = 1:9). [α] 20 D : (c = 1, CH 2 Cl 2 ). IR: (ATR), v ~ = 2942 cm 1 (m), 2842 (w), 1770 (s), 1591 (s), 1507 (s), 1485 (s), 1419 (s), 1208 (vs), 1102 (vs), 1025 (vs). MS: (EI, 70 ev): m/z (%) = 560 (100), 449 (45), 427 (3), 315 (98), 299 (39), 285 (56). 1 H-NMR: (360 MHz, CDCl 3 ): δ [ppm] = (m, 1 H), 3.11 (dd, 3 J = 8.1 Hz, 3 J = 6.6 Hz, 1 H), 3.82 (s, 6 H), 3.82 (s, 3 H), 4.02 (dd, 2 J = 9.3 Hz, 3 J = 6.0 Hz, 1 H), 4.34 (dd, 2 J = 9.3 Hz, 3 J = 7.3 Hz, 1 H), 4.58 (d, 3 J = 8.1 Hz, 1 H), 5.09 (d virt. t, 3 J = 17.1 Hz, J 0.9 Hz, 1 H), 5.14 (d virt. t, 3 J = 10.3 Hz, J 0.9 Hz, 1 H), 5.76 (ddd, 3 J = 17.1 Hz, 3 J = 10.3 Hz, 3 J = 8.3 Hz, 1 H), 6.01 (d, 2 J = 1.4 Hz, 1 H), 6.02 (d, 2 J = 1.4 Hz, 1 H), 6.58 (s, 2 H), 6.72 (s, 1 H), 6.89 (s, 1 H). 13 C-NMR: (90.6 MHz, CDCl 3 ): δ [ppm] = 43.6, 44.7, 49.5, 56.2, 60.9, 70.3, 102.6, 102.6, 105.7, 108.8, 117.9, (q, 1 J CF = 320 Hz), 127.6, 135.3, 135.6, 137.4, 140.8, 147.4, 147.6, 153.4, CHN: calcd: C: H: 4.14; found: C: H: ( )-4-Desoxy-4-methylene-podophyllotoxin (9): H C 23 H g/mol Me Me Me Triflate 6c (400 mg, 714 µmol, 1.00 eq.) was dissolved in 40 ml dry, oxygen-free MeCN (degased by ultrasonic purge with argon) and PPh 3 (56.2 mg, 214 µmol, 0.30 eq.), K 2 C 3 (296 mg, 2.14 mmol, 3.00 eq.) and Pd(Ac) 2 (16.0 mg, 71.4 µmol, 10 mol-%) were added in this order. The mixture was heated to 80 C (higher temperature led to further decomposition) and stirred at that temperature for 20 hours. After cooling to room temperature, the suspension was filtered over a short pad of silica, washed with additional 200 ml CH 2 Cl 2 and concentated under reduced pressure. The obtained crude product was purified by flash chromatography (2 15 cm, P:Et 2 = 2:8) to give 9 (170 mg, 414 µmol, 58%) as a white solid. R f : 0.49 (P:Et 2 = 1:9). [α] D 20 : 153 (c = 1, CHCl 3 ). m.p.: 107 C.

6 MS: (EI, 70 ev): m/z (%) = 410 (100), 395 (8), 364 (19), 334 (10), 242 (51). 1 H-NMR: (360 MHz, CDCl 3 ): δ [ppm] = 2.86 (dd, 3 J = 14.9 Hz, 3 J = 4.8 Hz, 1 H), 3.30 (ddd virt. t, 3 J = 14.9 Hz, 3 J = 10.5 Hz, 3 J = 7.1 Hz, 4 J 2.4 Hz, 1 H), 3.74 (s, 6 H), 3.80 (s, 3 H), 4.22 (dd, 2 J = 8.4 Hz, 3 J = 10.5 Hz, 1 H), 4.57 (dd, 2 J = 8.4 Hz, 3 J = 7.1 Hz, 1 H), 4.65 (d, 3 J = 4.8 Hz, 1 H), 4.70 (d, J = 2.4 Hz, 1 H), 5.54 (d, J = 2.4 Hz, 1 H), 5.97 (d, 2 J = 1.3 Hz, 1 H), 5.99 (d, 2 J = 1.3 Hz, 1 H), 6.36 (s, 2 H), 6.55 (s, 1 H), 7.22 (s, 1 H). 13 C-NMR: (90.6 MHz, CDCl 3 ): δ [ppm] = 37.7, 44.5, 47.3, 56.2, 60.7, 69.8, 101.5, 103.4, 105.5, 108.1, 110.2, 128.2, 132.3, 135.0, 137.2, 141.4, 147.6, 148.5, 152.6, ( )-Podophyllotoxon: [17] H C 22 H g/mol Me Me Me Alkene 9 (104 mg, 253 µmol, 1.00 eq.) and N-methylmorpholin-N-oxide (103 mg, 760 µmol, 3.00 eq.) were dissolved in 10 ml CH 2 Cl 2 and s 4 (4 wt-% in H 2, 81 µl, 3.2 mg, 12.7 µmol, 5 mol-%) was added. The solution was heavily stirred at room temperature and conversion was monitored by TLC. After aprox. four hours the reaction was complete and NaI 4 (108 mg, 507 µmol, 2.00 eq.) was added (depending on the quality of NaI 4 sometimes a second portion was necessary to achieve complete glycol cleavage). After 30 minutes the reaction was quenched by addition of saturated aqueous Na 2 S 2 3 (10 ml). The separated aqueous layer was extracted with CH 2 Cl 2 (2 10 ml). The combined organic layers were washed with saturated aqueous NaCl (10 ml), dried over Na 2 S 4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (2 15 cm, P:Et 2 = 1:9) to give ( )-Podophyllotoxon (99 mg, 240 µmol, 95%) as a white solid. R f : 0.40 (P:Et 2 = 1:9). [α] 20 D : 124 (c = 1, CHCl 3 ). m.p.: C. MS: (EI, 70 ev): m/z (%) = 412 (100), 367 (21), 336 (10), 168 (10), 153 (12). 1 H-NMR: (360 MHz, CDCl 3 ): δ [ppm] = 3.27 (dd, 3 J = 15.5 Hz, 3 J = 4.3 Hz, 1 H), (m, 1 H), 3.75 (s, 6 H), 3.81 (s, 3 H), 4.35 (dd, 2 J = 9.3 Hz, 3 J = 10.4 Hz, 1 H), 4.55

7 (dd, 2 J = 9.3 Hz, 3 J = 7.6 Hz, 1 H), 4.84 (d, 3 J = 4.3 Hz, 1 H), 6.08 (d, 2 J = 1.2 Hz, 1 H), 6.09 (d, 2 J = 1.2 Hz, 1 H), 6.38 (s, 2 H), 6.70 (s, 1 H), 7.55 (s, 1 H). 13 C-NMR: (90.6 MHz, CDCl 3 ): δ [ppm] = 43.5, 44.7, 46.7, 56.3, 60.7, 70.0, 102.4, 106.1, 107.7, 109.6, 128.2, 132.1, 137.8, 141.5, 148.1, 153.1, 153.2, 173.0, ( )-Podophyllotoxin (1): [18] H H C 22 H g/mol Me Me Me ( )-Podophyllotoxon (58 mg, 141 µmol, 1.00 eq.) was dissolved in 10 ml dry Et 2 and cooled to to 78 C. After addition of LiAlH(tBu) 3 (358 mg, 1.41 mmol, 10.0 eq.) the suspension was slowly warmed to room temperature without removing the cooling bath (18 hours), then the reaction was quenched by addition of 2 N HCl (10 ml). The separated aqueous layer was extracted with CH 2 Cl 2 (3 5 ml). The combined organic layers were washed with saturated aqueous NaCl (5 ml), dried over Na 2 S 4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography ( cm, P:EtAc = 1:9) to give ( )-Podophyllotoxin (1, 46 mg, 111 µmol, 79%) as a white solid in a diastereomeric mixture of 98:2 (Epipodophyllotoxin can be separated by recrystallization from ethanol/cyclohexane). R f : 0.41 (P:EtAc = 1:9). [α] 20 D : 103 (c = 0.41, EtH), Lit.: (c = 0.55, EtH 1 ), (c = 0.53, EtH 2 ), 104 (c = 0.36, EtH 3 ). m.p.: C. MS: (EI, 70 ev): m/z (%) = 414 (100), 181 (9), 168 (17). 1 H-NMR: (360 MHz, CDCl 3 ): δ [ppm] = 2.20 (bs, 1 H), (m, 1 H), 2.83 (dd, 3 J = 14.2 Hz, 3 J = 4.6 Hz, 1 H), 3.75 (s, 6 H), 3.81 (s, 3 H), 4.07 (virt. t, 3 J 9.2 Hz, 1 H), (m, 2 H), 4.76 (d, 3 J = 9.0 Hz, 1 H), 5.96 (d, 2 J = 1.3 Hz, 1 H), 5.98 (d, 2 J = 1.3 Hz, 1 H), 6.37 (s, 2 H), 6.50 (s, 1 H), 7.11 (s, 1 H). 1 D. B. Berkowitz, S. Choi, J.-H. Maeng, J. rg. Chem. 2000, 65, E. J. Bush, D. W. Jones, J. Chem. Soc. Perkin Trans , R. C. Andrews, S. J. Teague, A. I. Meyers, J. Am. Chem. Soc. 1988, 110,

8 13 C-NMR: (90.6 MHz, CDCl 3 ): δ [ppm] = 40.7, 44.1, 45.3, 56.3, 60.7, 71.3, 72.7, 101.4, 106.3, 108.3, 109.7, 131.1, 133.2, 135.4, 137.2, 147.6, 147.6, 152.6, HRMS: (EI): calcd for C 22 H 22 8 [M + ]: ; found:

9 ( )-Podophyllotoxin (1): ppm (t1) ppm (f1)

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