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1 Supporting Information Total Synthesis and Structural Reassignment of (±)-Cereoanhydride Zhiqiang Ren, Yu Hao, Xiangdong Hu* Department of Chemistry & Material Science, Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education of China, Northwest University, Xi an , China Table of Contents Experimental procedures and characterization data S-2 NMR spectra S-9 X-ray structure of 2 S-18 1

2 General thods: All commercially reactants don t need further purification. The solvents are appropriate first with the desiccant drying and distilled again before use. Tetrahydrofuran, 1,4-dioxane, and ethyl ether were distilled from sodium. Dichloromethane were distilled from CaH 2. Column chromatography was performed on silica gel ( mesh). 1 H NMR spectra were recorded on a 400 MHz NMR spectrometer and 13 C NMR spectra were recorded on a 100 MHz NMR spectrometer. IR spectra were recorded on a FT-IR spectrometer. 1. Preparation of compound 10 Br Mg, Et 2, 8, then HCl, DCM (83%) ipr ipr 9 ipr 8 10 A solution of the compound 9 (4.0 g, mmol) in Et 2 (20 ml) was added dropwise to a stirred mixture of Mg (585 mg, mmol) and Et 2 (8 ml) under nitrogen. Then, the mixture was refluxed for 30 minutes and a solution of 8 (2.4 g, mmol) in Et 2 (30 ml) was added dropwise. After further refluxing for 1-2 minutes, the mixture was quenched with saturated aqueous NH 4 Cl and extracted with EtAc. The organic layer was washed with saturated brine, and dried over anhydrous Na 2 S 4. The organic phase was concentrated by vacuum. The crude product was dissolved in CH 2 Cl 2 (50 ml) and aqueous HCl was added to the solution to make the solution ph=1-3. The solution was stirred at the room temperature for 3 hours, quenched with saturated aqueous NaHC 3, and extracted with CH 2 Cl 2. The organic layer was washed with brine, and dried over anhydrous Na 2 S 4. The organic phase was concentrated and purified by column chromatography (silica gel, petroleum ether ethyl acetate = 4:1), affording 10 as a yellow oil (3.0 g, 83%). IR (film): 3523, 2985, 1795, 1093, 775 cm -1 ; 1 H NMR (400MHz, CDCl 3 ) δ 5.44 (septet, J = 8 Hz, 1H), 2.20 (s, 3H), 1.50 (s, 6H), 1.44 (d, J = 8 Hz, 6H); 13 C NMR (100 MHz, CDCl 3 ) δ 205.8, 197.5, 194.2, 193.7, 184.0, 80.0, , 22.9, HRMS calcd for C 12 H 16 4 Na [M+Na]: ; found:

3 1) Castro, J. M.; Linares-Palomino, P. J.; Salido, S.; Altarejos, J.; Nogueras, M.; Sanches, A. Tetrahedron Lett. 2004, 45, ) Liebeskind, L. S.; Foste, B. S. J. Am. Chem. Soc. 1990, 112, Preparation of compound 11 H TBSCl imidazole DMAP TBS Br CH 2 Cl 2, 0 - rt 93% Br 7 11 The phenol 7 (2.0 g, mmol) was dissolved in CH 2 Cl 2 (35 ml) and cooled to 0 before addition of imidazole (1.2 g, mmol), DMAP (catalytic) and TBSCl (1.9 g, mmol). The mixture was stirred for 18 hours, quenched with saturated aqueous NaHC 3, and extracted with CH 2 Cl 2. The organic layer was dried over anhydrous Na 2 S 4, concentrated, and purified by column chromatography (silica gel, petroleum ether), affording 11 as a colorless oil (3.1 g, 93%). IR (film): 2931, 1568, 846, cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 6.94 (s, 1H), 6.82 (s, 1H), 6.59 (s, 1H), 2.27 (s, 3H), 0.99 (s, 9H), 0.21 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ) δ 156.4, 141.0, 125.3, 122.2, 120.5, 119.8, 25.7, 21.3, 18.3, HRMS calcd for C 13 H 21 BrSi [M+] , found: Roush, W. R.; Neitz, R. J. J. rg. Chem. 2004, 69, Preparation of compound 12 TBS Br n-buli THF, Et2, % 11 TBS 12 H ipr A solution of 11 (696 mg, 2.32 mmol) in THF (10 ml) was cold to -78, and n-buli (2.5 M, 2.61 mmol) was added under nitrogen. The solution was stirred at -78 for 10 minutes, and added dropwise to a solution of 10 (400 mg, 1.81 mmol) 3

4 in Et 2 (40 ml) precooled to -110 under nitrogen. The mixture was stirred for 5 minutes, quenched with saturated NH 4 Cl and extracted with EtAc. The organic phase was dried over anhydrous Na 2 S 4, concentrated, and purified by column chromatography (silica gel, petroleum ether : ethyl acetate = 4:1), affording 12 as a yellow oil (420 mg, 60%). IR (film): 3352, 2933, 1597, 1160, 839 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 6.90 (s, 1H), 6.71 (s, 1H), 6.60 (s, 1H), 4.68 (septet, J = 8 Hz, 1H), 2.25 (s, 3H), 2.29(s, 3H), 1.44 (s, 6H), 1.35 (d, J = 8 Hz, 3H), 1.00 (d, J = 8 Hz 3H), 0.96 (s, 9H), 0.16 (s, 6H); 13 C NMR (100MHz, CDCl3) δ 209.2, 189.5, 182.5, 155.9, 139.9, 138.1, 130.0, 120.8, 119.4, 114.2, 92.7, 79.2, 47.9, 26.0, 25.8, 23.0, 22.9, 22.8, 22.5, 21.7, 18.3, HRMS calcd for C 25 H 38 5 SiNa [M+Na]: ; found: ) Trost, B. M.; Thiel,. R.; Tsui, H. -C. J. Am. Chem. Soc. 2003, 125, ) Decker,. H. W.; Moore, H. W. J. rg. Chem. 1987, 52, Preparation of compound 13 TBS 12 H ipr toluene, 110 then DDQ 40% ipr 13 TBS A solution of 12 (100 mg, 0.23 mmol) in toluene (5 ml) was heated at 110 for 12 hours under nitrogen. The solution was cooled to room temperature, and DDQ (52 mg, 0.23 mmol) was added. It was allowed to stir at room temperature for 1 hour, and purified by column chromatography (silica gel, petroleum ether : ethyl acetate = 10:1), affording 13 as a reddish oil (40 mg, 40%). IR (film): 2931, 1596, 1091, 840 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 7.30 (s, 1H), 6.88 (s, 1H), 5.27 (septet, J = 4 Hz, 1H), 2.60 (s, 3H), 2.09 (s, 3H), 1.48 (s, 6H), 1.33 (d, J = 4 Hz, 6H), 0.98 (s, 9H), 0.25 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ) δ 204.7, 181.7, 178.0, 154.3, 151.5, 139.0, 134.7, 129.9, 124.1, 110.8, 71.0, 46.1, 21.0, 20.8, 20.3, 18.2, 18.0, HRMS calcd for 4

5 C 25 H 36 5 SiNa [M+Na]: ; found: ) nofrey, T. J.; Gomez, D.; Winters, M.; Moore, H. W. J. rg. Chem. 1997, 62, ) Liebeskind, L.S.; Iyer, S.; Jewell, C. F. J. rg. Chem., 1986, 51, Preparation of compound 6 TBS 12 H ipr Ac 2, DMAP Et 3 N CH 2 Cl 2, 0 - rt 95% TBS Ac ipr 6 12 (200 mg, 0.45 mmol) was dissolved in CH 2 Cl 2 (35 ml) and cooled to 0 before addition of Et 3 N (113 mg, 2.24 mmol), DMAP (6 mg) and Ac 2 (114 mg, 2.24 mmol) under nitrogen. The mixture was stirred for 12 hours at room temperature, quenched with saturated aqueous NaHC 3, and extracted with CH 2 Cl 2. The organic phase was dried over anhydrous Na 2 S 4, concentrated, and purified by column chromatography (silica gel, petroleum ether : EtAc = 6:1), affording 6 as a yellow oil (207 mg, 95%). IR (film): 2933,1619,1224,842 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 6.86 (s, 1H), 6.67 (s, 1H), 6.63 (s, 1H), 4.48 (septet, J = 8Hz, 1H), 2.30 (s, 3H), 2.29 (s, 3H), 2.22 (s, 3H), 1.45 (s, 3H), 1.42 (s, 3H), 1.27 (d, J = 8 Hz, 3H), 1.06 (d, J = 8Hz, 3H), 0.96 (s, 9H), 0.16 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ) δ 209.0, 182.9, 177.1, 169.6, 156.1, 140.2, 135.7, 131.1, 121.3, 118.9, 113.9, 96.2, 79.3, 47.9, 26.4, 25.7, 23.0, 22.8, 22.7, 22.6, 21.7, , HRMS calcd for C 27 H 40 6 SiNa [M+Na]: ; found: ) Pagar, V. V.; Jadhav, A. M.; Liu, R.-S. J. Am. Chem. Soc. 2011, 133, ) Asikainen, M.; Woodward, S. Tetrahedron. 2012, 68, Preparation of compound 18 5

6 TBS Ac ipr p-xylene 150, 85% H ipr Ac TBS 6 18 A solution of 6 (180 mg, 0.37 mmol) in p-xylene (5 ml) was heated at 150 for 2 hours under nitrogen. The solution was cooled to room temperature, and purified by column chromatography (silica gel, petroleum ether : ethyl acetate = 8:1), affording 18 as a white solid (153 mg, 85%). IR (film): 3511, 2931, 1768, 1197, 839 cm -1 ; 1 H NMR (400MHz, CDCl 3 ) δ 6.74 (s, 1H), 6.68 (s, 1H), 4.81 (septet, J = 4 Hz 1H), 2.77 (s, 3H), 2.39 (s, 3H), 1.61 (s, 3H), 1.50 (s, 3H), (m, 10H), 1.00 (s, 9H), 0.22 (s, 6H). 13 C NMR (100MHz, CDCl 3 ) δ 169.1, 153.9, 151.7, 144.5, 137.0, 130.5, 113.0, 112.1, 122.0, 113.9, 105.5, 74.0, 48.2, 25.8, 25.8, 25.5, 22.9, 20.7, 18.3, HRMS calcd for C 27 H 40 6 SiNa [M+Na]: ; found: lting point: Preparation of compound 5 H ipr Ac TBS TFA Et 3 SiH CH 2 Cl 2, 0, 86% ipr Ac TBS 18 5 To a solution of 18 (150 mg, 0.31 mmol) in CH 2 Cl 2 (5 ml) was added Et 3 SiH (178mg, 1.53 mmol), TFA (175mg, 1.53 mmol). The mixture was stirred at 0 for 10 minutes. The reaction was quenched with saturated aqueous NaHC 3 and extracted with CH 2 Cl 2. The organic phase was dried over anhydrous Na 2 S 4, concentrated, and purified by silica gel chromatography (ethyl acetate : petroleum ether=1:50) to yield 5 as a white solid (124 mg, 86%). IR (film): 3450, 2931, 1768, 1373, 842 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ) δ 6.73 (s, 1H), 6.66 (s, 1H), 4.82 (septet, J = 4 Hz, 1H), 4.42 (q, J = 8 Hz, 1H), 2.76 (s, 3H), 2.39 (s, 3H), (m, 4H), (m, 10H), 1.20 (s, 4H), 1.01 (s, 10H), 0.22 (s, 6H); 13 C NMR (100MHz, 6

7 CDCl 3 ) δ 169.3, 154.6, 153.8, 144.5, 137.3, 130.4, 122.3, 121.7, 113.6, 105.5, 88.8, 73.8, 44.8, 30.4, 25.9, 23.0, 21.8, 20.9, 18.4, 14.3, HRMS calcd for C 27 H 40 5 SiNa [M+Na]: ; found: lting point: ) Yao, X.; Xie, X.; Wang, C.; Zu, L. rg. Lett. 2015, 17, ) Kraus, G. A.; Molina, M. T.; Walling, J. A. J. rg. Chem. 1987, 52, Preparation of compound 4 5 ipr Ac TBS 1) LAH, THF, 0 2) CAN CH 3 CN/H 2 = 2/1 0 - rt two steps 65% 4 H To a solution of 5 (100 mg, 0.22 mmol) in THF (10 ml) precooled to 0 under nitrogen, LiAlH 4 (25 mg, 0.65 mmol) was carefully added. The mixture was stirred for 1-2 minutes, quenched with saturated aqueous NH 4 Cl, and extracted with Et 2. The organic phase was dried over anhydrous sodium sulfate and concentrated. The crude product was dissolved in acetonitrile (3 ml). To the solution above, a solution of CAN (298 mg 0.66 mmol) in water (1.5 ml) was added at 0. The mixture was stirred for 3 hours at room temperature before the addition of CH 2 Cl 2 (10 ml) and brine (20 ml). The combined organic layers were dried over anhydrous Na 2 S 4 and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (ethyl acetate : petroleum ether=1:2), affording 4 as a purple black solid (39 mg, 65%). IR (film): 2964, 1531, 1299, 796 cm -1 ; 1 H NMR (400 MHz, d 6 -DMS) δ (s, 1H), 7.16 (s, 1H), 6.83 (s, 1H), 4.61(q, J = 8 Hz, 1H), 2.45 (s, 3H), 1.36 (d, J = 8 Hz, 3H), 1.29 (s, 3H), 1.10 (s, 3H); 13 C NMR (100 MHz, d 6 -DMS) δ 181.6, 174.6, 170.9, 160.0, 140.2, 133.9, 123.5, 120.8, 116.3, 115.1, 91.7, 42.3, 25.4, 21.6, 20.1, HRMS calcd for C 16 H 16 4 Na [M+Na]: ; found: lting point: ) Nagaki, M.; Matsumoto, S.; Tsuri, T. J. rg. Chem. 2003, 68,

8 2) Kimachi, T.; Torii, E.; Kobayashi, Y.; Doe, M.; Ju-ichi, M. Chem. Pharm. Bull. 2011, 59, Preparation of cereoanhydride 2 4 H 1) MCPBA CH 2 Cl 2, 0 - rt 2) HCl, THF, rt two steps 30% C 2 H H H (±)-cereoanhydride (2) reassigned structure H A solution of m-cpba (85%, 166 mg, 0.82 mmol) in CH 2 Cl 2 (5 ml) was added into a solution of 4 (200 mg, 0.74 mmol) in CH 2 Cl 2 (10 ml) at 0. The resulting mixture was stirred for 2 hours at room temperature and concentrated. A solution of the residue in THF (5 ml), was mixed with 10% aqueous HCl (2 ml) at room temperature. The resulting mixture was stirred at room temperature for 48hours, concentrated and purified by chromatography on silica gel (ethyl acetate : petroleum ether=1:1), providing 2 as a white solid (66 mg, 30%). IR (film): 3315, 1714, 1373, 881 cm -1 ; 1 H NMR (400 MHz, CD 3 D) δ 6.95 (s, 1H), 6.93 (s, 1H), 4.21 (q, J = 8 Hz), 3.51 (s, 1H), 2.38 (s, 3H), 1.36 (d, J = 8 Hz, 3H), 1.28 (s, 6H); 13 C NMR (100 MHz, CD 3 D) δ 170.7, 170.4, 161.0, 137.4, 136.2, 131.0, 124.7, 113.1, 108.6, 87.4, 60.4, 43.8, 26.1, 17.6, 17.2, HRMS calcd for C 16 H 18 6 Na[M+Na]: ; found: lting point: ) Yang, R.-Y.; Kizer, D.; Wu, H.; Volckova, E.; Miao, X.-S.; Ali, S. M.; Tandon, M.; Savage, R. E.; Chan, T. C. K.; Ashwell, M. A. Bioorg. d. Chem. 2008, 16, ) Kato, K.; Sasaki, T.; Takayama, H.; Akita, H. Tetrahedron. 2003, 59,

9 1 H NMR spectrum of compound 10 (400 MHz, CDCl 3 ) 13 C NMR spectrum of compound 10 (100 MHz, CDCl 3 ) 9

10 1 H NMR spectrum of compound 11 (400 MHz, CDCl 3 ) 13 C NMR spectrum of compound 11 (100 MHz, CDCl 3 ) 10

11 1 H NMR spectrum of compound 12 (400 MHz, CDCl 3 ) 13 C NMR spectrum of compound 12 (100 MHz, CDCl 3 ) 11

12 1 H NMR spectrum of compound 13 (400 MHz, CDCl 3 ) 13 C NMR spectrum of compound 13 (100 MHz, CDCl 3 ) 12

13 1 H NMR spectrum of compound 6 (400 MHz, CDCl 3 ) 13 C NMR spectrum of compound 6 (100 MHz, CDCl 3 ) 13

14 1 H NMR spectrum of compound 18 (400 MHz, CDCl 3 ) 13 C NMR spectrum of compound 18 (100 MHz, CDCl 3 ) 14

15 1 H NMR spectrum of compound 5 (400 MHz, CDCl 3 ) 13 C NMR spectrum of compound 5 (100 MHz, CDCl 3 ) 15

16 1 H NMR spectrum of compound 4 (400 MHz, d 6 -DMS) 13 C NMR spectrum of compound 4 (100 MHz, d 6 -DMS) 16

17 1 H NMR spectrum of compound 2 (400 MHz, CD 3 D) 13 C NMR spectrum of compound 2 (100 MHz, CD 3 D) 17

18 X-ray structure of 2 Datablock: xb9552 Bond precision: C-C = A Wavelength= Cell: a=11.970(6) b=16.000(8) c=8.190(4) alpha=90 beta=90 gamma=90 Temperature: 296 K Calculated Reported Volume (13) (14) Space group P c a 21 Pca2(1) Hall group P 2c -2ac? Moiety formula C16 H18 6? Sum formula C16 H18 6 C16 H18 6 Mr Dx,g cm Z 4 4 Mu (mm-1) F F h,k,lmax 15,20,10 14,20,10 Nref 3661[ 1963] 3396 Tmin,Tmax 0.964,0.969 Tmin Correction method= Not given Data completeness= 1.73/0.93 Theta(max)= R(reflections)= ( 2475) wr2(reflections)= (

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