Total Synthesis of ( )-Cryptocaryol A
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- Arabella Gillian Neal
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Total Synthesis of ( )-Cryptocaryol A Luiz C. Dias,* Paula K. Kuroishi, and Emílio C. de Lucca Jr. Instituto de Química, Universidade Estadual de Campinas, , C.P. 6154, Campinas, SP, Brazil * ldias@iqm.unicamp.br Table of Contents Figure S1. 1 H NMR spectrum of 8 (250 MHz; C 6 D 6 ). Figure S2. 13 C NMR spectrum of 8 (62.5 MHz; C 6 D 6 ). Figure S3. 13 C NMR spectrum (DEPT 135) of 8 (62.5 MHz; C 6 D 6 ). Figure S4. IR and HRMS spectra of 8. Figure S5. 1 H NMR spectrum of 11 (600 MHz; C 6 D 6 ). Figure S6. 13 C NMR spectrum of 11 (125 MHz; C 6 D 6 ). Figure S7. 13 C NMR spectrum (DEPT 135) of 11 (125 MHz; C 6 D 6 ). Figure S8. IR and HRMS spectra of 11. Figure S9. 1 H NMR spectrum of 12 (500 MHz; CDCl 3 ). Figure S C NMR spectrum of 12 (125 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 12 (125 MHz; CDCl 3 ). Figure S12. IR and HRMS spectra of 12. Figure S13. 1 H NMR spectrum of 13 (400 MHz; CDCl 3 ). Figure S C NMR spectrum of 13 (100 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 13 (100 MHz; CDCl 3 ). Figure S16. IR and HRMS spectra of 13. S5 S6 S6 S7 S8 S9 S9 S10 S11 S12 S12 S13 S14 S15 S15 S16 S1
2 Figure S17. 1 H NMR spectrum of 14 (500 MHz; CDCl 3 ). Figure S C NMR spectrum of 14 (125 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 14 (125 MHz; CDCl 3 ). Figure S20. COSY contour map for 14. Figure S21. HSQC contour map for 14. Figure S22. HMBC contour map for 14. Figure S23. IR and HRMS spectra of 14. Figure S24. 1 H NMR spectrum of 6 (250 MHz; CDCl 3 ). Figure S C NMR spectrum of 6 (62.5 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 6 (62.5 MHz; CDCl 3 ). Figure S27. IR and HRMS spectra of 6. Figure S28. 1 H NMR spectrum of 15 (500 MHz; C 6 D 6 ). Figure S C NMR spectrum of 15 (125 MHz; C 6 D 6 ). Figure S C NMR spectrum (DEPT 135) of 15 (125 MHz; C 6 D 6 ). Figure S31. IR and HRMS spectra of 15. Figure S32. 1 H NMR spectrum of 16 (500 MHz; CDCl 3 ). Figure S C NMR spectrum of 16 (125 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 16 (125 MHz; CDCl 3 ). Figure S35. IR and HRMS spectra of 16. Figure S36. 1 H NMR spectrum of 17 (500 MHz; CDCl 3 ). Figure S C NMR spectrum of 17 (125 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 17 (125 MHz; CDCl 3 ). Figure S39. IR and HRMS spectra of 17. Figure S40. 1 H NMR spectrum of 18 (500 MHz; OD). Figure S C NMR spectrum of 18 (125 MHz; OD). S17 S18 S18 S19 S20 S21 S22 S23 S24 S24 S25 S26 S27 S27 S28 S29 S30 S30 S31 S32 S33 S33 S34 S35 S36 S2
3 Figure S C NMR spectrum (DEPT 135) of 18 (125 MHz; OD). Figure S43. COSY contour map for 18. Figure S44. HSQC contour map for 18. Figure S45. HMBC contour map for 18. Figure S46. IR and HRMS spectra of 18. Figure S47. 1 H NMR spectrum of 19 (500 MHz; CDCl 3 ). Figure S C NMR spectrum of 19 (125 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 19 (125 MHz; CDCl 3 ). Figure S50. IR and HRMS spectra of 19. Figure S51. 1 H NMR spectrum of 20 (600 MHz; CDCl 3 ). Figure S C NMR spectrum of 20 (150 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 20 (150 MHz; CDCl 3 ). Figure S54. IR and HRMS spectra of 20. Figure S55. 1 H NMR spectrum of 2 (250 MHz; CDCl 3 ). Figure S C NMR spectrum of 2 (62.5 MHz; CDCl 3 ). Figure S C NMR spectrum (DEPT 135) of 2 (62.5 MHz; CDCl 3 ). Figure S58. IR and HRMS spectra of 2. Figure S59. 1 H NMR spectrum of 1 (500 MHz; OD). Figure S C NMR spectrum of 1 (125 MHz; OD). Figure S C NMR spectrum (DEPT 135) of 1 (125 MHz; OD). Figure S62. COSY contour map for 1. Figure S63. HSQC contour map for 1. Figure S64. HMBC contour map for 1. Figure S65. IR and HRMS spectra of 1. Table 1. 1 H and 13 C NMR chemical shifts for cryptocaryol A. S36 S37 S38 S39 S40 S41 S42 S42 S43 S44 S45 S45 S46 S47 S48 S48 S49 S50 S51 S51 S52 S53 S54 S55 S56 S3
4 Attempts to optimize de aldol reaction Scheme S1. Figure S66. Scheme S2. Scheme S3. Scheme S4. Scheme S5. Scheme S6. Scheme S7. Scheme S8. Scheme S9. S57 S57 S57 S58 S59 S59 S60 S60 S61 S61 S62 S4
5 Acquisition Time (sec) Comment Paula PKK8 C6D6 250 MHz mar14pkkh1 Date 14 Mar :54:14 File Name C:\Users\Usuário\Documents\Unicamp\strado\Espectros RMN\250\mar14pkkH1 (PKK8)_001001r Frequency (MHz) Nucleus 1H Number of Transients 12 Original Points Count Points Count Pulse Sequence zg30 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Benzene-d6 O OPMB Figure S1. 1 H NMR spectrum of 8 (250 MHz; C 6 D 6 ). S5
6 Acquisition Time (sec) Comment Paula PKK8 C6D6 250 MHz mar14pkkc1 13C Date 15 Mar :30:38 File Name C:\Users\Usuário\Documents\Unicamp\strado\Espectros RMN\250\mar14pkkC1 (PKK8)_002001r Frequency (MHz) Nucleus 13C Number of Transients Original Points Count 8192 Points Count Pulse Sequence zgpg30 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Benzene-d Figure S2. 13 C NMR spectrum of 8 (62.5 MHz; C 6 D 6 ). Acquisition Time (sec) Comment Paula PKK8 C6D6 250 MHz mar14pkkc1 C13DEPT135 Date 15 Mar :31:56 File Name C:\Users\Usuário\Documents\Unicamp\strado\Espectros RMN\250\mar14pkkC1 (PKK8)_001001r Frequency (MHz) Nucleus 13C Number of Transients 3072 Original Points Count 8192 Points Count Pulse Sequence dept135 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Figure S3. 13 C NMR spectrum (DEPT 135) of 8 (62.5 MHz; C 6 D 6 ). S6
7 %Transmittance Title cial do Brasil (GMT-3:00) Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK8.SP Date Stamp mon jul 15 16:25: Hora oficial do Brasil (GMT-3:00) Date mon jul 15 16:25: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) Figure S4. IR spectrum of S7
8 Acquisition Time (sec) Date 15 Apr :47:14 File Name F:\strado\Espectros RMN\600\abr15pkkH1 (PKK12)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Benzene-d6 OH 11 O OPMB Figure S5. 1 H NMR spectrum of 11 (600 MHz; C 6 D 6 ). S8
9 Acquisition Time (sec) Comment Paula PKK12 c6d6 AV500 MHz abr05pkkh1-13c Date 05 Apr :56:24 File Name F:\strado\Espectros RMN\500\abr05pkkH1 (PKK12)_002001r Frequency (MHz) Nucleus 13C Number of Transients 849 Original Points Count Points Count Pulse Sequence zgpg30 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Benzene-d Figure S6. 13 C NMR spectrum of 11 (125 MHz; C 6 D 6 ). Acquisition Time (sec) Comment Paula PKK12 c6d6 AV500 MHz abr05pkkh1 - dept 135 Date 05 Apr :56:18 File Name F:\strado\Espectros RMN\500\abr05pkkH1 (PKK12)_003001r Frequency (MHz) Nucleus 13C Number of Transients 320 Original Points Count Points Count Pulse Sequence dept135 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Figure S7. 13 C NMR spectrum (DEPT 135) of 11 (125 MHz; C 6 D 6 ). S9
10 Relative Abundance %Transmittance Title cial do Brasil (GMT-3:00) Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK12.SP Date Stamp mon jul 15 18:05: Hora oficial do Brasil (GMT-3:00) Date mon jul 15 18:05: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C011 #29 RT: 0.44 AV: 1 NL: 3.30E7 T: FTMS + p ESI Full ms [ ] C 17 H 24 O 4 Na ppm C C H 24 O 4 Na ppm C C 2 H 24 O 4 Na ppm m/z Figure S8. IR and HRMS spectra of S10
11 Acquisition Time (sec) Comment Paula "PKK13" cdcl3/av500mhz abr09pkkh1 Date 17 Dec :23:40 File Name F:\strado\Espectros RMN\500\abr09pkkH1 (PKK13)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) TMS OH OH OPMB Figure S9. 1 H NMR spectrum of 12 (500 MHz; CDCl 3 ). S11
12 Acquisition Time (sec) Comment Paula "PKK13" cdcl3/av500mhz abr09pkkh1-13c Date 10 Apr :57:32 File Name C:\Users\Usuário\Documents\Unicamp\strado\Espectros RMN\500\abr09pkkH1 (PKK13)_002001r Frequency (MHz) Nucleus 13C Number of Transients 3072 Original Points Count Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 12 (125 MHz; CDCl 3 ). Acquisition Time (sec) Comment Paula "PKK13" cdcl3/av500mhz abr09pkkh1 -Dept135 Date 10 Apr :37:06 File Name C:\Users\Usuário\Documents\Unicamp\strado\Espectros RMN\500\abr09pkkH1 (PKK13)_003001r Frequency (MHz) Nucleus 13C Number of Transients 1024 Original Points Count Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 12 (125 MHz; CDCl 3 ). S12
13 Relative Abundance %Transmittance Title cial do Brasil (GMT-3:00) Comment Amostra 000 por LQOS data segunda-feira, julho Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK13.SP Date Stamp mon jul 15 17:41: Hora oficial do Brasil (GMT-3:00) Date mon jul 15 17:41: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C012 #7 RT: 0.10 AV: 1 NL: 3.09E7 T: FTMS + p ESI Full ms [ ] C 17 H 26 O 4 Na ppm C C H 26 O 4 Na ppm C C 2 H 26 O 4 Na ppm m/z Figure S12. IR and HRMS spectra of 12. S13
14 Acquisition Time (sec) Date 30 Apr :00:54 File Name F:\strado\Espectros RMN\400\abr30pkkH1 (PKK17)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) O O OPMB TMS Figure S13. 1 H NMR spectrum of 13 (400 MHz; CDCl 3 ). S14
15 Acquisition Time (sec) Date 30 Apr :57:36 File Name F:\strado\Espectros RMN\400\abr30pkkH1 (PKK17)_002001r Frequency (MHz) Nucleus 13C Number of Transients 1024 Original Points Count Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 13 (100 MHz; CDCl 3 ). Acquisition Time (sec) Date 30 Apr :10:52 File Name F:\strado\Espectros RMN\400\abr30pkkH1 (PKK17)_003001r Frequency (MHz) Nucleus 13C Number of Transients 473 Original Points Count Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 13 (100 MHz; CDCl 3 ). S15
16 Relative Abundance %Transmittance Title cial do Brasil (GMT-3:00) Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK17.SP Date Stamp mon jul 15 17:58: Hora oficial do Brasil (GMT-3:00) Date mon jul 15 17:58: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C014 #7 RT: 0.10 AV: 1 NL: 4.68E7 T: FTMS + p ESI Full ms [ ] C 20 H 30 O 4 Na ppm C 19 13C H 30 O 4 Na ppm C 18 13C 2 H 30 O 4 Na ppm m/z Figure S16. IR and HRMS spectra of 13. S16
17 Acquisition Time (sec) Comment Paula - PKK 15 - CDCl3 - Avance 500 MHz - abr12pkkh2-1h Date 15 Apr :43:16 File Name F:\strado\Espectros RMN\500\abr12pkkH2 (PKK16)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) OH O PMP O TMS Figure S17. 1 H NMR spectrum of 14 (500 MHz; CDCl 3 ). S17
18 Acquisition Time (sec) Comment Paula - PKK 15 - CDCl3 - Avance 500 MHz - abr12pkkh2-13c Date 12 Apr :43:16 File Name F:\strado\Espectros RMN\500\abr12pkkH2 (PKK15)_002001r Frequency (MHz) Nucleus 13C Number of Transients 512 Original Points Count Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 14 (125 MHz; CDCl 3 ). Acquisition Time (sec) Comment Paula - PKK 15 - CDCl3 - Avance 500 MHz - abr12pkkh2 - DEPT 135 Date 12 Apr :23:06 File Name F:\strado\Espectros RMN\500\abr12pkkH2 (PKK15)_003001r Frequency (MHz) Nucleus 13C Number of Transients 256 Original Points Count Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 14 (125 MHz; CDCl 3 ). S18
19 Figure S20. COSY contour map for 14. S19
20 Figure S21. HSQC contour map for 14. S20
21 Figure S22. HMBC contour map for 14. S21
22 Relative Abundance %Transmittance Title cial do Brasil (GMT-3:00) Comment Amostra 003 por LQOS data segunda-feira, julho Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK15.SP Date Stamp mon jul 15 17:49: Hora oficial do Brasil (GMT-3:00) Date mon jul 15 17:49: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C013 #8 RT: 0.11 AV: 1 NL: 9.09E6 T: FTMS + p ESI Full ms [ ] C 17 H 24 O 4 Na ppm C C H 24 O 4 Na ppm C C 2 H 24 O 4 Na ppm m/z Figure S23. IR and HRMS spectra of 14. S22
23 Acquisition Time (sec) Comment PKK69 250MHz nov27pkkh2 Date 27 Nov :45:12 File Name F:\strado\Espectros RMN\250\nov27pkkH2 (PKK69)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) TMS O O O OPMB Figure S24. 1 H NMR spectrum of 6 (250 MHz; CDCl 3 ). S23
24 Acquisition Time (sec) Comment PKK69 250MHz nov24pkkc1 Date 06 Mar :43:06 File Name C:\Users\Usuário\Documents\Unicamp\strado\Espectros RMN\250\nov24pkkC1 (PKK69 C)_001001r Frequency (MHz) Nucleus 13C Number of Transients Original Points Count 8192 Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 6 (62.5 MHz; CDCl 3 ). Acquisition Time (sec) Comment PKK69 250MHz nov24pkkc1 dept135 Date 25 Nov :38:44 File Name F:\strado\Espectros RMN\250\nov24pkkC1 (PKK69)_002001r Frequency (MHz) Nucleus 13C Number of Transients 5000 Original Points Count 8192 Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 6 (62.5 MHz; CDCl 3 ). S24
25 Relative Abundance %Transmittance Title brasileiro de verão (GMT-2:00) Comment Amostra 014 por LQOS data sexta-feira, dezembro Origin brasileiro de verão (GMT-2:00) File Name E:\MESTRADO\IV PAULA\PKK69.SP Date Stamp fri dec 20 10:43: Horário brasileiro de verão (GMT-2:00) Date fri dec 20 10:43: Horário brasileiro de verão (GMT-2:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C002 #16 RT: 0.25 AV: 1 NL: 7.32E7 T: FTMS + p ESI Full ms [ ] C 20 H 30 O 5 Na ppm C C H 30 O 5 Na ppm C 18 13C 2 H 30 O 5 Na ppm m/z Figure S27. IR and HRMS spectra of 6. S25
26 Acquisition Time (sec) Comment Paula - PKK 72 - C6D6 - Avance 500 MHz - dez02pkkh1-1h Date 03 Dec :28:20 File Name E:\strado\Espectros RMN\500\dez02pkkH1 (PKK72)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Benzene-d6 OH O O O OPMB Figure S28. 1 H NMR spectrum of 15 (500 MHz; C 6 D 6 ). S26
27 Acquisition Time (sec) Comment Paula - PKK 72 - C6D6 - Avance 500 MHz - dez02pkkh1-13c Date 03 Dec :28:30 File Name E:\strado\Espectros RMN\500\dez02pkkH1 (PKK72)_002001r Frequency (MHz) Nucleus 13C Number of Transients 919 Original Points Count Points Count Pulse Sequence zgpg30 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Benzene-d Figure S C NMR spectrum of 15 (125 MHz; C 6 D 6 ). Acquisition Time (sec) Comment Paula - PKK 72 - C6D6 - Avance 500 MHz - dez02pkkh1 - DEP 135 Date 03 Dec :28:40 File Name E:\strado\Espectros RMN\500\dez02pkkH1 (PKK72)_003001r Frequency (MHz) Nucleus 13C Number of Transients 512 Original Points Count Points Count Pulse Sequence dept135 Solvent BENZENE-D6 Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 15 (125 MHz; C 6 D 6 ). S27
28 Relative Abundance %Transmittance Title brasileiro de verão (GMT-2:00) Comment Amostra 006 por LQOS data sexta-feira, dezembro Origin brasileiro de verão (GMT-2:00) File Name E:\MESTRADO\IV PAULA\PKK72.SP Date Stamp fri dec 20 10:07: Horário brasileiro de verão (GMT-2:00) Date fri dec 20 10:07: Horário brasileiro de verão (GMT-2:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C003 #53 RT: 0.80 AV: 1 NL: 9.34E7 T: FTMS + p ESI Full ms [ ] C 24 H 36 O 6 Na ppm C 23 13C H 36 O 6 Na ppm m/z Figure S31. IR and HRMS spectra of C 22 13C 2 H 36 O 6 Na ppm S28
29 Acquisition Time (sec) Comment Paula "PKK-74" cdcl3/av500mhz dez09pkkh1 Date 10 Dec :08:14 File Name E:\strado\Espectros RMN\500\dez09pkkH1 (PKK74)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d OH OH O O OPMB Figure S32. 1 H NMR spectrum of 16 (500 MHz; CDCl 3 ). S29
30 Acquisition Time (sec) Comment Paula "PKK-98" cdcl3/ Av500MHz mar18pkkc1 Date 19 Mar :39:16 File Name F:\strado\Espectros RMN\500\mar18pkkC1_001001r Frequency (MHz) Nucleus 13C Number of Transients 2048 Original Points Count Points Count Pulse Sequence zgig Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 16 (125 MHz; CDCl 3 ). Acquisition Time (sec) Comment Paula "PKK-74" cdcl3/av500mhz dez09pkkh1 - Dept135 Date 10 Dec :08:38 File Name E:\strado\Espectros RMN\500\dez09pkkH1 (PKK74)_003001r Frequency (MHz) Nucleus 13C Number of Transients 1024 Original Points Count Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 16(125 MHz; CDCl 3 ). S30
31 Relative Abundance %Transmittance Title brasileiro de verão (GMT-2:00) Comment Amostra 007 por LQOS data sexta-feira, dezembro Origin brasileiro de verão (GMT-2:00) File Name E:\MESTRADO\IV PAULA\PKK74.SP Date Stamp fri dec 20 10:12: Horário brasileiro de verão (GMT-2:00) Date fri dec 20 10:12: Horário brasileiro de verão (GMT-2:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C004 #20 RT: 0.30 AV: 1 NL: 1.04E8 T: FTMS + p ESI Full ms [ ] C 24 H 38 O 6 Na ppm C 23 13C H 38 O 6 Na ppm C 22 13C 2 H 38 O 6 Na ppm m/z Figure S35. IR and HRMS spectra of 16. S31
32 Acquisition Time (sec) Comment Paula - PKK99 - CDCl3 - Av 500 MHz - mar20pkkh2 Date 20 Mar :54:36 File Name F:\strado\Espectros RMN\500\mar20pkkH2 (PKK99)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) TMS O O O O OPMB Figure S36. 1 H NMR spectrum of 17 (500 MHz; CDCl 3 ). S32
33 Acquisition Time (sec) Comment Paula - PKK99 - CDCl3 - Av 500 MHz - mar20pkkh2 13C Date 20 Mar :22:54 File Name F:\strado\Espectros RMN\500\mar20pkkH2 (PKK99)_002001r Frequency (MHz) Nucleus 13C Number of Transients 512 Original Points Count Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 17 (125 MHz; CDCl 3 ). Acquisition Time (sec) Comment Paula - PKK99 - CDCl3 - Av 500 MHz - mar20pkkh2 DEPT135 Date 20 Mar :23:08 File Name F:\strado\Espectros RMN\500\mar20pkkH2 (PKK99)_003001r Frequency (MHz) Nucleus 13C Number of Transients 128 Original Points Count Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 17 (125 MHz; CDCl 3 ). S33
34 Relative Abundance %Transmittance Title cial do Brasil (GMT-3:00) Comment Amostra 003 por LQOS data quarta-feira, abril Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK99_1.SP Date Stamp wed apr 16 15:05: Hora oficial do Brasil (GMT-3:00) Date wed apr 16 15:05: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C005 #16 RT: 0.24 AV: 1 NL: 3.94E7 T: FTMS + p ESI Full ms [ ] C 27 H 42 O 6 Na ppm C 26 13C H 42 O 6 Na ppm C 25 13C 2 H 42 O 6 Na ppm m/z Figure S39. IR and HRMS spectra of 17. S34
35 Acquisition Time (sec) Comment Paula "PKK-102" cd3od/av500mhz mar25pkkh2 Date 26 Mar :34:36 File Name \\nmrsparc.iqm.unicamp.br\espectros\avance500\2014\mar14\luiz Carlos\mar25pkkH2_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent OD Sweep Width (Hz) Temperature (degree C) thanol-d4 OH OH OH OH OPMB Figure S40. 1 H NMR spectrum of 18 (500 MHz; OD). S35
36 Acquisition Time (sec) Comment Paula "PKK-102" cd3od/av500mhz mar25pkkh2-13c Date 26 Mar :34:48 File Name \\nmrsparc.iqm.unicamp.br\espectros\avance500\2014\mar14\luiz Carlos\mar25pkkH2_002001r Frequency (MHz) Nucleus 13C Number of Transients 2048 Original Points Count Points Count Pulse Sequence zgpg30 Solvent OD Sweep Width (Hz) Temperature (degree C) thanol-d Figure S C NMR spectrum of 18 (125 MHz; OD). Acquisition Time (sec) Comment Paula "PKK-102" cd3od/av500mhz mar25pkkh2 - Dept135 Date 26 Mar :34:58 File Name \\nmrsparc.iqm.unicamp.br\espectros\avance500\2014\mar14\luiz Carlos\mar25pkkH2_003001r Frequency (MHz) Nucleus 13C Number of Transients 512 Original Points Count Points Count Pulse Sequence dept135 Solvent OD Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 18 (125 MHz; OD). S36
37 Figure S43. COSY contour map for 18. S37
38 Figure S44. HSQC contour map for 18. S38
39 Figure S45. HMBC contour map for 18. S39
40 Relative Abundance %Transmittance Title cial do Brasil (GMT-3:00) Comment Amostra 001 por LQOS data sexta-feira, outubro Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK102.SP Date Stamp fri oct 17 17:06: Hora oficial do Brasil (GMT-3:00) Date fri oct 17 17:06: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C008 #33 RT: 0.50 AV: 1 NL: 1.50E8 T: FTMS + p ESI Full ms [ ] C 21 H 34 O 6 Na ppm C 20 13C H 34 O 6 Na ppm C 19 13C 2 H 34 O 6 Na ppm m/z Figure S46. IR and HRMS spectra of 18. S40
41 Acquisition Time (sec) Comment Paula "PKK-100" cdcl3/av500mhz mar25pkkh1 Date 26 Mar :34:24 File Name \\nmrsparc.iqm.unicamp.br\espectros\avance500\2014\mar14\luiz Carlos\mar25pkkH1_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d O O O O OH Figure S47. 1 H NMR spectrum of 19 (500 MHz; CDCl 3 ). S41
42 Acquisition Time (sec) Comment Paula - PKK100 - CDCl3 - Av 500 MHz - mar20pkkh1 13C Date 20 Mar :53:58 File Name F:\strado\Espectros RMN\500\mar20pkkH1 (PKK100)_002001r Frequency (MHz) Nucleus 13C Number of Transients 512 Original Points Count Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 19 (125 MHz; CDCl 3 ). Acquisition Time (sec) Comment Paula - PKK100 - CDCl3 - Av 500 MHz - mar20pkkh1 DEPT135 Date 20 Mar :54:10 File Name F:\strado\Espectros RMN\500\mar20pkkH1 (PKK100)_003001r Frequency (MHz) Nucleus 13C Number of Transients 128 Original Points Count Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 19 (125 MHz; CDCl 3 ). S42
43 Relative Abundance %Transmittance Title brasileiro de verão (GMT-2:00) Comment recuperado de PKK77 Origin brasileiro de verão (GMT-2:00) File Name F:\MESTRADO\IV PAULA\PKK76.SP Date Stamp fri dec 20 09:38: Horário brasileiro de verão (GMT-2:00) Date fri dec 20 09:38: Horário brasileiro de verão (GMT-2:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C006 #24 RT: 0.36 AV: 1 NL: 3.39E7 T: FTMS + p ESI Full ms [ ] C 19 H 34 O 5 Na ppm C 18 13C H 34 O 5 Na ppm m/z Figure S50. IR and HRMS spectra of 19. S43
44 Acquisition Time (sec) Date 07 Jan :25:18 File Name \\nmrsparc.iqm.unicamp.br\espectros\avance600\2014\jan14\luiz Carlos\jan07pkkH1_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d O O O O O Figure S51. 1 H NMR spectrum of 20 (600 MHz; CDCl 3 ). S44
45 Acquisition Time (sec) Date 07 Jan :58:08 File Name \\nmrsparc.iqm.unicamp.br\espectros\avance600\2014\jan14\luiz Carlos\jan07pkkH1_002001r Frequency (MHz) Nucleus 13C Number of Transients 1877 Original Points Count Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 20 (150 MHz; CDCl 3 ). Acquisition Time (sec) Date 07 Jan :42:42 File Name \\nmrsparc.iqm.unicamp.br\espectros\avance600\2014\jan14\luiz Carlos\jan07pkkH1_003001r Frequency (MHz) Nucleus 13C Number of Transients 1024 Original Points Count Points Count Pulse Sequence deptsp135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 20 (150 MHz; CDCl 3 ). S45
46 Relative Abundance %Transmittance Title brasileiro de verão (GMT-2:00) Comment Amostra 001 por LQOS data sexta-feira, janeiro Origin brasileiro de verão (GMT-2:00) File Name E:\MESTRADO\IV PAULA\PKK77.SP Date Stamp fri jan 24 10:40: Horário brasileiro de verão (GMT-2:00) Date fri jan 24 10:40: Horário brasileiro de verão (GMT-2:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C007 #8 RT: 0.12 AV: 1 NL: 5.81E7 T: FTMS + p ESI Full ms [ ] C 19 H 32 O 5 Na ppm C 18 13C H 32 O 5 Na ppm C C 2 H 32 O 5 Na ppm m/z Figure S54. IR and HRMS spectra of 20. S46
47 Acquisition Time (sec) Comment PKK82 CDCl3 250MHz jan16pkkh1 Date 16 Jan :02:30 File Name F:\strado\Espectros RMN\250\jan16pkkH1 (PKK82)_001001r Frequency (MHz) Nucleus 1H Number of Transients 16 Original Points Count Points Count Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d O O O O O O OEt Figure S55. 1 H NMR spectrum of 2 (250 MHz; CDCl 3 ). S47
48 Acquisition Time (sec) Comment PKK82 CDCl3 250MHz jan16pkkc1 Date 24 Jan :16:36 File Name F:\strado\Espectros RMN\250\jan16pkkC1 (PKK82)correto_002001r Frequency (MHz) Nucleus 13C Number of Transients Original Points Count 8192 Points Count Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Chloroform-d Figure S C NMR spectrum of 2 (62.5 MHz; CDCl 3 ). Acquisition Time (sec) Comment PKK82 CDCl3 250MHz jan16pkkc1 dept135 Date 24 Jan :16:18 File Name F:\strado\Espectros RMN\250\jan16pkkC1 (PKK82)correto_001001r Frequency (MHz) Nucleus 13C Number of Transients 1024 Original Points Count 8192 Points Count Pulse Sequence dept135 Solvent CHLOROFORM-D Sweep Width (Hz) Temperature (degree C) Figure S C NMR spectrum (DEPT 135) of 2 (62.5 MHz; CDCl 3 ). S48
49 Relative Abundance %Transmittance Title cial do Brasil (GMT-3:00) Comment Amostra 002 por LQOS data sexta-feira, outubro Origin cial do Brasil (GMT-3:00) File Name E:\MESTRADO\IV PAULA\PKK112.SP Date Stamp fri oct 17 17:12: Hora oficial do Brasil (GMT-3:00) Date fri oct 17 17:12: Hora oficial do Brasil (GMT-3:00) Technique Infrared Instrument Spectrum Two Spectral Region IR X Axis Wavenumber (cm-1) Y Axis %Transmittance Spectrum Range Points Count 3451 Data Spacing Wavenumber (cm-1) C009 #7 RT: 0.10 AV: 1 NL: 2.37E6 T: FTMS + p ESI Full ms [ ] C 22 H 36 O 7 Na ppm C 21 13C H 36 O 7 Na ppm C 24 H 30 O 6 Na ppm m/z Figure S58. IR and HRMS spectra of C C H 30 O 6 Na ppm S49
50 Acquisition Time (sec) Date 07 Mar :39:24 File Name F:\strado\Espectros RMN\500\mar07pkkH1 (PKK96)_001001r Frequency (MHz) Nucleus 1H Number of Transients 32 Original Points Count Points Count Pulse Sequence zg30 Solvent OD Sweep Width (Hz) Temperature (degree C) thanol-d4 O O OH OH OH OH OH ( )-cryptocaryol A (1) Figure S59. 1 H NMR spectrum of 1 (500 MHz; OD). S50
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Supporting Information for: Synthesis of two novel indolo[3,2-b]carbazole derivatives with aggregation-enhanced emission property Wen-Bin Jia, Hao-Wei Wang, Long-Mei Yang, Hong-Bo Lu, Lin Kong, Yu-Peng
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250/- 100/- 400/- 1000/- 1500/- D 2 O Exchange 300/- 150/- 400/- 1100/- 2000/- 13 C, DEPT, 19F or
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Supplementary Figures a) Starting materials b) After 1 hour exchange c) After 5 days exchange d) After pump down e) After SiO 2 plug Supplementary Figure 1 Self-assembly of [Na + o-me 2-1.1.1]BArF -. 1
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Supporting Information Facile Synthesis of Rhodamine-Based Highly Sensitive and Fast Responsive Colorimetric and Off-On Fluorescent Reversible Chemosensors for Hg2+: Preparation of a Fluorescent Thin Film
Location. Datum. Survey. information. Etrometa. Step Gauge. Description. relative to Herne Bay is -2.72m. The site new level.
Tide Gauge Location OS: 616895E 169377N WGS84: Latitude: 51 o 22.919196 N Longitude: 01 o 6.9335907 E Instrument Type Etrometa Step Gauge Benchmarks Benchmark TGBM = 5.524m above Ordnance Datum Newlyn
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Location. Datum. Survey. information. Etrometa. Step Gauge. Description. relative to Herne Bay is -2.72m. The site new level.
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SUPPLEMENTARY INFORMATION
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ANALYTICAL REPORT 1. RTI-111 (C16H19Cl2NO2) methyl 3-(3,4-dichlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
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