Appendix 1
Spectra Relevant to Chapter 2:
Total Syntheses of Ent-Kauranoids
(–)-Trichorabdal A and (–)-Longikaurin E
jtsy-viii-101 Sample Name: jtsy-viii-101 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-viii-101 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: May 31 2012 Sample #13, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 2.500 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7127407 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 40 sec
1.03 1.05 2.09 0.99 1.03 3.09 1.08 1.00 1.06 1.08 4.13 0.48 3.21 3.24 1.76 1.16 3.22 2.93 9.85 6.08
ppm 1 2 3 4 5 6 7 8 9 10
O
HO O
Me Me T B SO S1
jtsy-viii-101 Sample Name: jtsy-viii-101 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-viii-101 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: May 31 2012 Sample #13, Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 512 repetitions OBSERVE C13, 125.6528709 MHz DECOUPLE H1, 499.7152303 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 1.0 Hz FT size 65536 Total time 17 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
HO O
Me Me T B SO S1
Sample Name: jtsy-viii-097 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-viii-097 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: May 30 2012 Sample #48, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 2.500 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7127410 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 40 sec
0.94 0.96 0.99 2.03 0.94 1.01 2.00 3.97 2.01 1.04 0.96 2.08 2.01 1.05 0.99 2.98 2.91 9.41 6.03
ppm 1 2 3 4 5 6 7 8 9 10
O
O O
Me Me T B SO 66
Sample Name: jtsy-viii-097 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-viii-097 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: May 30 2012 Sample #48, Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 512 repetitions OBSERVE C13, 125.6528718 MHz DECOUPLE H1, 499.7152303 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 17 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
O O
Me Me T B SO 66
Sample Name: jtsy-vii-089char Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-vii-089char FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Mar 15 2012 Sample #20, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 2.500 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7225128 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 40 sec
1.08 2.24 1.03 1.03 1.03 1.08 1.08 1.00 1.03 5.45 2.17 1.09 4.49 2.05 1.16 4.55 4.30 8.84 2.98 3.00
ppm 1 2 3 4 5 6 7 8 9 10
O
H
HO H Me T B SO Me H O 67
Sample Name: jtsy-vii-089char Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-vii-089char FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Mar 15 2012 Sample #20, Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 512 repetitions OBSERVE C13, 125.6553299 MHz DECOUPLE H1, 499.7250019 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 17 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
H
HO H Me T B SO Me H O 67
Sample Name: jtsy-vii-191char Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-vii-191char FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Feb 14 2012 Sample #14, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 2.500 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7225195 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 40 sec
1.05 2.14 1.01 1.01 1.02 1.01 1.02 1.03 1.02 3.14 1.00 1.01 5.32 2.13 1.04 3.35 1.36 3.87 3.12 9.25 3.03 3.09
ppm 1 2 3 4 5 6 7 8 9 10
O
H
MO MO H Me T B SO Me H O 68
Sample Name: jtsy-vii-191char Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-vii-191char FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Feb 14 2012 Sample #14, Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 512 repetitions OBSERVE C13, 125.6553270 MHz DECOUPLE H1, 499.7250019 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 17 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
H
MO MO H Me T B SO Me H O 68
Sample Name: jtsy-vii-231plug Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-vii-231plug FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Feb 28 2012 Sample #20, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 2.500 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7225125 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 40 sec
1.01 2.00 0.98 0.98 0.91 1.00 0.97 1.95 2.93 0.92 0.88 0.95 1.93 1.89 3.84 4.37 2.99 3.68 9.37 10.19 5.77 2.76 3.40
ppm 1 2 3 4 5 6 7 8 9 10
O
MO MO H Me T B SO Me H OTBS 64
Sample Name: jtsy-vii-231plug Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-vii-231plug FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Feb 28 2012 Sample #20, Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 1700 repetitions OBSERVE C13, 125.6553261 MHz DECOUPLE H1, 499.7250019 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 1.0 Hz FT size 65536 Total time 58 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
MO MO H Me T B SO Me H OTBS 64
Sample Name: jtsy-ix-081B-f23-39 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-081B-f23-39 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Jan 23 2013 Sample #46, Operator: yeomanjo Relax. delay 2.000 sec Pulse 45.0 degrees Acq. time 3.000 sec Width 7995.2 Hz 8 repetitions OBSERVE H1, 499.7049152 MHz DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 0 min 40 sec
0.99 0.97 2.10 2.03 0.90 0.99 1.14 3.01 0.90 1.02 2.02 2.04 1.06 0.94 0.98 1.01 3.07 1.07 2.64 3.21 3.01 10.43 6.73
ppm 1 2 3 4 5 6 7 8 9 10
O
O O MO M
H T B SO Me Me 69
Sample Name: jtsy-vii-125 Data Collected on: daytona.caltech.edu-inova500 Archive directory: Sample directory: FidFile: jtsy-vii-125-c13 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Jan 12 2012 Temp. 25.0 C / 298.1 K Operator: yeomanjo Relax. delay 0.100 sec Pulse 45.0 degrees Acq. time 1.043 sec Width 31421.8 Hz 48000 repetitions OBSERVE C13, 125.6871022 MHz DECOUPLE H1, 499.8513810 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 2.0 Hz FT size 65536 Total time 15 hr, 14 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
O O MO M
H T B SO Me Me 69
O
O O MO M
H T B SO Me Me 69
O
O O MO M
H T B SO Me Me 69
O
O O MO M
H T B SO Me Me 69
O
O O MO M
H T B SO Me Me 69
Sample Name: jtsy-ix-199f30-35 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-199f30-35 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Jun 13 2013 Sample #46, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 3.000 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7049153 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 44 sec
0.93 0.99 1.03 0.95 0.98 1.00 1.00 3.00 0.90 1.90 1.99 3.01 1.10 1.18 0.90 1.07 1.04 6.35 2.52 1.08 3.38 3.07 10.32 3.41 3.28
ppm 1 2 3 4 5 6 7 8 9 10
O
Me H
MO MO H Me T B SO Me H O 79
O
Sample Name: jtsy-ix-199f30-35 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-199f30-35 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Jun 13 2013 Sample #46, Operator: yeomanjo Relax. delay 0.100 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 3000 repetitions OBSERVE C13, 125.6509014 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 2.0 Hz FT size 65536 Total time 57 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
Me H
MO MO H Me T B SO Me H O 79
O
Sample Name: jtsy-ix-133Bf15-23 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-133Bf15-23 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Mar 5 2013 Sample #32, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 3.000 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7049151 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 44 sec
0.96 2.00 0.86 0.92 0.91 0.91 3.17 0.84 1.94 1.06 1.91 1.08 0.90 1.53 1.33 3.19 1.13 1.79 3.37 12.80 3.03 3.01
ppm 1 2 3 4 5 6 7 8 9 10
O
O O MO M
O H T B SO Me Me 71
Sample Name: jtsy-ix-133Bf15-23 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-133Bf15-23 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Mar 5 2013 Sample #32, Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 1000 repetitions OBSERVE C13, 125.6509033 MHz DECOUPLE H1, 499.7074131 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 1.0 Hz FT size 65536 Total time 34 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
O O MO M
O H T B SO Me Me 71
Sample Name: jtsy-ix-107 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-107 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Feb 13 2013 Sample #39, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 3.000 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7049151 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 44 sec
0.92 0.96 0.99 1.99 0.87 0.94 0.90 0.88 3.20 1.00 0.86 0.91 0.92 0.93 0.88 1.03 1.02 2.04 3.19 2.42 3.31 3.67 9.73 3.17 2.96
ppm 1 2 3 4 5 6 7 8 9 10
O
O O MO M
O H T B SO Me Me 72
Sample Name: jtsy-ix-107 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-107 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Feb 13 2013 Sample #39, Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 1000 repetitions OBSERVE C13, 125.6509014 MHz DECOUPLE H1, 499.7074131 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 1.0 Hz FT size 65536 Total time 34 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
O O MO M
O H T B SO Me Me 72
Sample Name: jtsy-ix-115f16-35 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-115f16-35 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Feb 15 2013 Sample #39, Operator: yeomanjo Relax. delay 10.000 sec Pulse 45.0 degrees Acq. time 3.000 sec Width 8000.0 Hz 8 repetitions OBSERVE H1, 499.7049151 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 65536 Total time 1 min 44 sec
1.01 1.01 1.01 1.01 1.00 1.01 0.99 1.02 1.00 1.01 1.06 1.07 1.10 2.15 1.09 1.83 3.91 2.53 3.25 3.64
ppm 1 2 3 4 5 6 7 8 9 10
O
O OH
O H HO Me Me S2
Sample Name: jtsy-ix-115f16-35 Data Collected on: daytona.caltech.edu-inova500 Archive directory: Sample directory: FidFile: jtsy-ix-115f16-35 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Feb 17 2013 Temp. 25.0 C / 298.1 K Operator: yeomanjo Relax. delay 0.100 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 20000 repetitions OBSERVE C13, 125.6871032 MHz DECOUPLE H1, 499.8513810 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 3.0 Hz FT size 65536 Total time 6 hr, 20 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O O OH
O H HO Me Me S2
Sample Name: jtsy-ix-143prep Data Collected on: fid.caltech.edu-inova600 Archive directory: /home/yeomanjo/vnmrsys/data Sample directory: jtsy-ix-143prep FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: pyridine Data collected on: Mar 13 2013 Temp. 60.0 C / 333.1 K Operator: yeomanjo Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.708 sec Width 9594.6 Hz 8 repetitions OBSERVE H1, 599.6348295 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 0 min 22 sec
0.95 0.85 0.96 1.00 1.02 0.52 1.18 0.92 0.91 0.98 0.91 3.15 0.82 1.00 1.00 2.01 0.99 3.06 3.11
ppm 1 2 3 4 5 6 7 8 9 10
O
O OH
O H H Me Me O (– )-t ri ch o ra b d a l A (1 2 )
Sample Name: jtsy-ix-143prep Data Collected on: daytona.caltech.edu-inova500 Archive directory: Sample directory: FidFile: jtsy-ix-143prep-c13 Pulse Sequence: CARBON (s2pul) Solvent: pyridine Data collected on: Mar 15 2013 Temp. 60.0 C / 333.1 K Operator: yeomanjo Relax. delay 0.100 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 13000 repetitions OBSERVE C13, 125.6870252 MHz DECOUPLE H1, 499.8512260 MHz Power 39 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 5.0 Hz FT size 65536 Total time 4 hr, 7 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O O OH
O H H Me Me O (– )-t ri ch o ra b d a l A (1 2 )
O
O OH
O H H Me Me O (– )-t ri ch o ra b d a l A (1 2 )
O O OH
O H H Me Me O (– )-t ri ch o ra b d a l A (1 2 )
O
O OH
O H H Me Me O (– )-t ri ch o ra b d a l A (1 2 )
O
O OH
O H H Me Me O (– )-t ri ch o ra b d a l A (1 2 )
Sample Name: VWM2-007-c2f13-24 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-007-c2f13-24 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: May 1 2013 Sample #27, Operator: vmak Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 2.621 sec Width 6250.0 Hz 16 repetitions OBSERVE H1, 499.7049153 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 0 min 58 sec
2.00 1.94 1.05 1.00 1.02 2.15 2.02 1.08 1.96 1.08 1.01 3.04 1.73 3.16 1.08 3.13 2.93
ppm 1 2 3 4 5 6 7 8 9 10
O
O OH
H HO Me Me 73
Sample Name: VWM2-007-c2f13-24 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-007-c2f13-24 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: May 1 2013 Sample #27, Operator: vmak Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 1000 repetitions OBSERVE C13, 125.6509033 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 1.0 Hz FT size 65536 Total time 34 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O O OH
H HO Me Me 73
VWM2-019 Sample Name: VWM2-019 Data Collected on: fid.caltech.edu-inova600 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-019 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: CDCl3 Data collected on: May 9 2013 Temp. 25.0 C / 298.1 K Operator: vmak Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.705 sec Width 9611.9 Hz 8 repetitions OBSERVE H1, 599.6357305 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 0 min 22 sec
0.94 2.07 0.80 1.04 1.02 1.05 1.10 1.13 1.87 1.05 0.90 1.18 2.00 4.17 1.09 1.17 3.00 3.18
ppm 1 2 3 4 5 6 7 8 9 10
O O OH
H H Me Me 74
O
Sample Name: VWM2-019-comb Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-019-comb FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: May 9 2013 Sample #22, Operator: vmak Relax. delay 0.500 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 2250 repetitions OBSERVE C13, 125.6509043 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 4.0 Hz FT size 65536 Total time 58 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O
O OH
H H Me Me 74
O
Sample Name: VWM2-017-f14-19 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-017-f14-19 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: May 7 2013 Sample #35, Operator: vmak Relax. delay 2.000 sec Pulse 45.0 degrees Acq. time 2.048 sec Width 8000.0 Hz 32 repetitions OBSERVE H1, 499.7049153 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 2 min 10 sec
0.93 1.00 2.07 0.77 1.04 0.98 1.08 1.00 1.00 2.13 3.12 2.96 1.08 6.57 1.84 3.09 3.13
ppm 1 2 3 4 5 6 7 8 9 10
O O OAc
H H Me Me 75
O
Sample Name: VWM2-021-comb Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-021-comb FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: May 9 2013 Sample #21, Operator: vmak Relax. delay 0.500 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 2250 repetitions OBSERVE C13, 125.6509033 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 4.0 Hz FT size 65536 Total time 58 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O O OAc
H H Me Me 75
O
Sample Name: VWM2-033c Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-033c FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: May 17 2013 Sample #33, Operator: vmak Relax. delay 2.000 sec Pulse 45.0 degrees Acq. time 2.621 sec Width 6250.0 Hz 32 repetitions OBSERVE H1, 499.7049149 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 2 min 28 sec
0.96 1.04 0.99 1.07 0.97 0.98 0.98 2.08 1.03 1.08 2.20 3.14 1.06 1.10 3.42 3.09 2.13 3.01 3.02
ppm 1 2 3 4 5 6 7 8 9 10
OAc
H Me Me 76
O
OH OH
Sample Name: VWM2-033c Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-033c FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: May 17 2013 Sample #33, Operator: vmak Relax. delay 0.100 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 3000 repetitions OBSERVE C13, 125.6509004 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 57 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
OAc
H Me Me 76
O
OH OH
Sample Name: VWM2-025-652013 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-025-652013 FidFile: PROTON02 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Jun 5 2013 Sample #36, Operator: vmak Relax. delay 2.000 sec Pulse 45.0 degrees Acq. time 2.621 sec Width 6250.0 Hz 128 repetitions OBSERVE H1, 499.7049153 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 9 min 53 sec
1.00 1.00 0.99 2.04 2.11 2.04 1.01 2.26 3.21 1.08 1.07 1.13 2.11 3.19 1.07 1.07 3.00 2.93
ppm 1 2 3 4 5 6 7 8 9 10
OAc
H Me Me 77
O OH
Sample Name: VWM2-025-652013 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-025-652013 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Jun 5 2013 Sample #36, Operator: vmak Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 8000 repetitions OBSERVE C13, 125.6509021 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 4 hr, 33 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
OAc
H Me Me 77
O OH
VWM3-063 Sample Name: VWM3-063 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM3-063 FidFile: PROTON05 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Jan 21 2014 Sample #18, Operator: vmak Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 3.000 sec Width 8000.0 Hz 32 repetitions OBSERVE H1, 499.6951455 MHz DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 2 min 8 sec
0.97 1.00 1.00 1.05 1.00 1.03 1.02 0.98 0.99 1.06 1.05 1.02 4.22 1.21 1.06 2.32 4.34 1.69 1.66 3.35 3.23
ppm 1 2 3 4 5 6 7 8 9 10
O
O OAc
H HO Me Me 78
VWM3-063 Sample Name: VWM3-063 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM3-063 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Jan 21 2014 Sample #18, Operator: vmak Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 5000 repetitions OBSERVE C13, 125.6484443 MHz DECOUPLE H1, 499.6976415 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 2.0 Hz FT size 65536 Total time 2 hr, 50 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
O O OAc
H HO Me Me 78
Sample Name: VWM2-063-f24-41 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-063-f24-41 FidFile: PROTON01 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Jun 13 2013 Sample #22, Operator: vmak Relax. delay 2.000 sec Pulse 45.0 degrees Acq. time 2.621 sec Width 6250.0 Hz 64 repetitions OBSERVE H1, 499.7049153 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 4 min 56 sec
0.97 1.00 0.99 1.00 1.01 0.94 2.15 1.03 2.13 1.06 2.99 1.02 1.06 2.28 2.00 3.83 3.01 3.06
ppm 1 2 3 4 5 6 7 8 9 10
OAc
O H Me Me 79
O
OH OH
Sample Name: VWM2-043-f26-36 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-043-f26-36 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: May 24 2013 Sample #34, Operator: vmak Relax. delay 0.100 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 3100 repetitions OBSERVE C13, 125.6509011 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 1.0 Hz FT size 65536 Total time 59 min
ppm 0 20 40 60 80 100 120 140 160 180 200 220
OAc
O H Me Me 79
O
OH OH
Sample Name: VWM2-067-c2 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-067-c2 FidFile: PROTON06 Pulse Sequence: PROTON (s2pul) Solvent: cdcl3 Data collected on: Jun 23 2013 Sample #35, Operator: vmak Relax. delay 2.000 sec Pulse 45.0 degrees Acq. time 2.621 sec Width 6250.0 Hz 128 repetitions OBSERVE H1, 499.7049153 MHz DATA PROCESSING Line broadening 0.2 Hz FT size 32768 Total time 9 min 53 sec
0.99 1.00 1.00 0.99 1.02 0.97 1.04 0.91 0.99 1.02 1.06 1.02 2.99 1.05 1.01 2.21 2.04 2.84 3.02 3.06
ppm 1 2 3 4 5 6 7 8 9 10
OAc
O H Me Me (– )-l o n g ika u ri n E (1 1 )
O
OH OH
Sample Name: VWM2-067-c2 Data Collected on: indy.caltech.edu-inova500 Archive directory: /home/vmak/vnmrsys/data Sample directory: VWM2-067-c2 FidFile: CARBON01 Pulse Sequence: CARBON (s2pul) Solvent: cdcl3 Data collected on: Jun 22 2013 Sample #20, Operator: vmak Relax. delay 1.000 sec Pulse 45.0 degrees Acq. time 1.042 sec Width 31446.5 Hz 12500 repetitions OBSERVE C13, 125.6509014 MHz DECOUPLE H1, 499.7074131 MHz Power 40 dB continuously on WALTZ-16 modulated DATA PROCESSING Line broadening 0.5 Hz FT size 65536 Total time 7 hr, 7 min
