VII. Supporting appendix
7.5 NMR spectra
Appendix 7.5-X Figure 1. 1H NMR (400 MHz, CDCl3) of nat-21 ...158 Figure 2. 13C NMR (150 MHz, CDCl3) of nat-21 ...159 Figure 3. 1H NMR (600 MHz, CDCl3) of 28 ...160 Figure 4. 13C NMR (150 MHz, CDCl3) of 28 ...161 Figure 5. 1H NMR (600 MHz, CDCl3) of 29 ...162 Figure 6. 13C NMR (150 MHz, CDCl3) of 29 ...163 Figure 7. 1H NMR (600 MHz, CDCl3) of 31 ...164 Figure 8. 13C NMR (150 MHz, CDCl3) of 31 ...165 Figure 9. 1H NMR (600 MHz, CDCl3) of 33 ...166 Figure 10. 13C NMR (150 MHz, CDCl3) of 33 ...167 Figure 11. 1H NMR (500 MHz, CDCl3) of 36 ...168 Figure 12. 13C NMR (125 MHz, CDCl3) of 36 ...169 Figure 13. 1H NMR (600 MHz, CDCl3) of 37 ...170 Figure 14. 13C NMR (150 MHz, CDCl3) of 37 ...171 Figure 15. 1H NMR (600 MHz, CDCl3) of 38 ...172 Figure 16. 13C NMR (150 MHz, CDCl3) of 38 ...173 Figure 17. 1H NMR (600 MHz, CDCl3) of 39 ...174 Figure 18. 13C NMR (150 MHz, CDCl3) of 39 ...175 Figure 19. 1H NMR (600 MHz, CDCl3) of 40 ...176 Figure 20. 13C NMR (150 MHz, CDCl3) of 40 ...177 Figure 21. 1H NMR (400 MHz, CDCl3) of 45 ...178 Figure 22. 13C NMR (150 MHz, CDCl3) of 45 ...179 Figure 23. 1H NMR (400 MHz, CDCl3) of 46 ...180 Figure 24. 13C NMR (125 MHz, CDCl3) of 46 ...181 Figure 25. 1H NMR (400 MHz, CDCl3) of 47 ...182 Figure 26. 13C NMR (125 MHz, CDCl3) of 47 ...183 Figure 27. 1H NMR (400 MHz, CDCl3) of 48 ...184 Figure 28. 13C NMR (125 MHz, CDCl3) of 48 ...185 Figure 29. 1H NMR (400 MHz, CDCl3) of 49 ...186 Figure 30.13C NMR (125 MHz, CDCl3) of 49 ...187 Figure 31. 1H NMR (400 MHz, CDCl3) of 50 ...188 Figure 32.13C NMR (125 MHz, CDCl3) of 50 ...189 Figure 33.1H NMR (400 MHz, CDCl3) of 51 ...190 Figure 34.13C NMR (125 MHz, CDCl3) of 51 ...191
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Appendix 7.5-155
Figure 35.1H NMR (400 MHz, CDCl3) of 52 ...192 Figure 36.13C NMR (125 MHz, CDCl3) of 52 ...193 Figure 37. 1H NMR (400 MHz, CDCl3) of 53 ...194 Figure 38. 13C NMR (125 MHz, CDCl3) of 53 ...195 Figure 39. 1H NMR (400 MHz, CDCl3) of epi-53 ...196 Figure 40. 13C NMR (125 MHz, CDCl3) of epi-53...197 Figure 41. 1H NMR (500 MHz, CDCl3) of 62 ...198 Figure 42. 13C NMR (125 MHz, CDCl3) of 62 ...199 Figure 43. 1H NMR (400 MHz, CDCl3) of 63 ...200 Figure 44. 13C NMR (125 MHz, CDCl3) of 63 ...201 Figure 45. 1H NMR (400 MHz, CDCl3) of nat-67 ...202 Figure 46. 13C NMR (150 MHz, CDCl3) of nat-67 ...203 Figure 47. 1H NMR (400 MHz, CDCl3) of nat-68 ...204 Figure 48. 1H NMR (400 MHz, CDCl3) of 70 ...205 Figure 49. 13C NMR (125 MHz, CDCl3) of 70 ...206 Figure 50. 1H NMR (400 MHz, CDCl3) of 72 ...207 Figure 51. 13C NMR (125 MHz, CDCl3) of 72 ...208 Figure 52. 1H NMR (400 MHz, CDCl3) of 73 ...209 Figure 53. 13C NMR (125 MHz, CDCl3) of 73 ...210 Figure 54. 1H NMR (400 MHz, DMSO-d6) of 74 ...211 Figure 55. 13C NMR (125 MHz, DMSO-d6) of 74 ...212 Figure 56. 1H NMR (400 MHz, CDCl3) of 75 ...213 Figure 57. 13C NMR (150 MHz, CDCl3) of 75 ...214 Figure 58. 1H NMR (400 MHz, CDCl3) of 76 ...215 Figure 59. 13C NMR (150 MHz, CDCl3) of 76 ...216 Figure 60. 1H NMR (400 MHz, DMSO-d6) of 77 ...217 Figure 61. 13C NMR (125 MHz, DMSO-d6) of 77 ...218 Figure 62. 1H NMR (400 MHz, CDCl3) of 78 ...219 Figure 63. 13C NMR (100 MHz, CDCl3) of 78 ...220 Figure 64. 1H NMR (400 MHz, CDCl3) of 79 ...221 Figure 65. 13C NMR (150 MHz, CDCl3) of 79 ...222 Figure 66. 1H NMR (600 MHz, CDCl3) of 80 ...223 Figure 67. 13C NMR (150 MHz, CDCl3) of 80 ...224 Figure 68. 1H NMR (400 MHz, CDCl3) of 81 ...225 Figure 69. 13C NMR (150 MHz, CDCl3) of 81 ...226 Figure 70. 1H NMR (400 MHz, DMSO-d6) of 91 ...227
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Appendix 7.5-156
Figure 71. 13C NMR (125 MHz, DMSO-d6) of 91 ...228 Figure 72. 1H NMR (400 MHz, CDCl3) of 92 ...229 Figure 73. 13C NMR (100 MHz, CDCl3) of 92 ...230 Figure 74. 1H NMR (500 MHz, CDCl3) of 93 ...231 Figure 75. 13C NMR (100 MHz, CDCl3) of 93 ...232 Figure 76. 1H NMR (400 MHz, CDCl3) of 95 ...233 Figure 77. 13C NMR (100 MHz, CDCl3) of 95 ...234 Figure 78. 1H NMR (400 MHz, CDCl3) of 97 ...235 Figure 79. 13C NMR (100 MHz, CDCl3) of 97 ...236 Figure 80. 1H NMR (400 MHz, CDCl3) of 99 ...237 Figure 81. 13C NMR (125 MHz, CDCl3) of 99 ...238 Figure 82. 1H NMR (400 MHz, CDCl3) of 100 ...239 Figure 83. 13C NMR (125 MHz, CDCl3) of 100 ...240 Figure 84. 1H NMR (400 MHz, CDCl3) of 101 ...241 Figure 85. 13C NMR (125 MHz, CDCl3) of 101 ...242 Figure 86. 1H NMR (400 MHz, DMSO-d6) of 102 ...243 Figure 87. 13C NMR (125 MHz, DMSO-d6) of 20 ...244 Figure 88. 1H NMR (400 MHz, CDCl3) of 108 ...245 Figure 89. 13C NMR (150 MHz, CDCl3) of 108 ...246 Figure 90. 1H NMR (400 MHz, CDCl3) of 109 ...247 Figure 91. 13C NMR (100 MHz, CDCl3) of 109 ...248 Figure 92. 1H NMR (400 MHz, DMSO-d6) of 110 ...249 Figure 93. 13C NMR (150 MHz, DMSO-d6) of 110 ...250 Figure 94. 1H NMR (400 MHz, DMSO-d6) of 111 ...251 Figure 95. 13C NMR (150 MHz, CD3CN) of 111 ...252 Figure 96. 1H NMR (400 MHz, DMSO-d6) of 112 ...253 Figure 97. 13C NMR (150 MHz, DMSO-d6) of 112 ...254 Figure 98. 1H NMR (400 MHz, DMSO-d6) of 113 ...255 Figure 99. 13C NMR (150 MHz, DMSO-d6) of 113 ...256 Figure 100. 1H NMR (400 MHz, CDCl3) of 115 ...257 Figure 101. 13C NMR (150 MHz, CDCl3) of 115 ...258 Figure 102. 1H NMR (600 MHz, CDCl3) of 116 ...259 Figure 103. 13C NMR (150 MHz, CDCl3) of 116 ...260 Figure 104. 1H NMR (400 MHz, DMSO-d6) of 117 ...261 Figure 105. 13C NMR (100 MHz, DMSO-d6) of 117 ...262 Figure 106. 1H NMR (400 MHz, CDCl3) of 118 ...263
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Appendix 7.5-157
Figure 107. 13C NMR (150 MHz, CDCl3) of 118 ...264 Figure 108. 1H NMR (400 MHz, DMSO-d6) of 122 ...265 Figure 109. 13C NMR (150 MHz, DMSO-d6) of 122 ...266 Figure 110. 1H NMR (600 MHz, DMSO-d6) of 123 ...267 Figure 111. 13C NMR (150 MHz, DMSO-d6) of 123 ...268 Figure 112. 1H NMR (600 MHz, CDCl3) of 130 ...269 Figure 113. 13C NMR (150 MHz, CDCl3) of 130 ...270 Figure 114. 1H NMR (600 MHz, DMSO-d6) of 131 ...271 Figure 115. 13C NMR (150 MHz, DMSO-d6) of 131 ...272 Figure 116. 1H NMR (600 MHz, DMSO-d6) of 132 ...273 Figure 117. 13C NMR (150 MHz, DMSO-d6) of 132 ...274 Figure 118. 1H NMR (900 MHz, DMSO-d6) of 133 ...275 Figure 119. 13C NMR (225 MHz, DMSO-d6) of 133 ...276 Figure 120. 1H-13C HSQC (225 MHz, DMSO-d6) of 133 ...277 Figure 121. HMBC (225 MHz, DMSO-d6) of 133 ...278 Figure 122. NOESY (900 MHz, DMSO-d6) of 133 ...279 Figure 123. 1H NMR (800 MHz, DMSO-d6) of 134 ...280 Figure 124. 13C NMR (200 MHz, DMSO-d6) of 134 ...281 Figure 125. HSQC (200 MHz, DMSO-d6) of 134 ...282 Figure 126. HMBC (200 MHz, DMSO-d6) of 134 ...283 Figure 127. NOESY (800 MHz, DMSO-d6) of 134 ...284 Figure 128. 1H NMR (600 MHz, CDCl3) of 135 ...285 Figure 129. 13C NMR (150 MHz, CDCl3) of 135 ...286 Figure 130. 1H NMR (600 MHz, CDCl3) of nat-136 ...287 Figure 131. 13C NMR (150 MHz, CDCl3) of nat-136 ...288 Figure 132. 1H NMR (400 MHz, CDCl3) of 137 ...289 Figure 133. 13C NMR (100 MHz, CDCl3) of 137 ...290
Batiste Dissertation Appendix 7.5
Appendix 7.5-158 Figure 1. 1H NMR (400 MHz, CDCl3) of nat-21
1H δ LiteratureMult, J values1H δ SynthesisMult, J values 0.88m0.82-0.89br m 1.30m 1.31m 1.38d, J = 7.2 Hz1.38d, J = 7.2 Hz 1.39d, J = 7.4 Hz1.39d, J = 7.5 Hz 1.41d, J = 7.4 Hz1.41d, J = 7.3 Hz 1.45d, J = 7.3 Hz1.45d, J = 7.4 Hz 1.59d, J = 7.3 Hz1.59d, J = 7.0 Hz 1.78m1.73-1.90br m 2.89s2.89s 2.91s2.91s 2.96s2.96s 3.01s3.01s 3.18s3.18s 4.56q, J = 7.3 Hz4.56q, J = 7.3 Hz 5.11dd, J = 10.6, 2.5 Hz5.11dd, J = 11.0, 2.4 Hz 5.30q, J = 7.4 Hz5.3q, J = 7.3 Hz 5.32dd, J = 10.1, 3.3 Hz5.32dd, J = 9.9, 3.3 Hz 5.36dd, J = 9.0, 5.3 Hz5.36dd, J = 8.5, 5.0 Hz 5.40q, J = 7.2 Hz5.4q, J = 7.2 Hz 5.42m5.42m (overlapping) 5.45dd, J = 8.4, 5.3 Hz5.45dd, J = 8.4, 5.4 Hz 5.53q, J = 7.3 Hz5.53q, J = 7.3 Hz 5.54q, J = 7.4 Hz5.54q, J = 7.5 Hz
1.06-1.31br m
Batiste Dissertation Appendix 7.5
Appendix 7.5-159 Figure 2. 13C NMR (150 MHz, CDCl3) of nat-21
13 C Literature values13 C Synthesis valuesDifference13 C Literature values13 C Synthesis valuesDifference 13.88 (3C)13.890.0131.231.160.04 13.913.950.0531.36 (2C)31.320.04 13.93140.0731.4 (3C)31.390.01 1414.10.131.531.460.04 14.214.2051.551.470.03 14.814.8051.7651.630.13 1515051.8551.720.13 15.915.880.0251.9451.870.07 22.39 (3C)22.39054.454.40 22.42 (2C)22.42070.770.650.05 24.76 (2C)24.740.0270.870.720.08 24.8224.8207170.910.09 24.8324.960.1371.371.220.08 25.125.070.0371.671.50.1 29.429.450.05169.2169.20 30.6630.650.01169.3169.260.04 30.7330.710.02169.8169.790.01 30.9230.830.09169.9 (2C)169.870.03 30.9730.870.1170169.920.08 30.9830.930.05170.8 (2C)170.710.09 3130.970.031711710 31.131.090.01171.2171.30.1
Batiste Dissertation Appendix 7.5
Appendix 7.5-160 Figure 3. 1H NMR (600 MHz, CDCl3) of 28
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Appendix 7.5-161 Figure 4. 13C NMR (150 MHz, CDCl3) of 28
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Appendix 7.5-162 Figure 5. 1H NMR (600 MHz, CDCl3) of 29
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Appendix 7.5-163 Figure 6. 13C NMR (150 MHz, CDCl3) of 29
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Appendix 7.5-164 Figure 7. 1H NMR (600 MHz, CDCl3) of 31
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Appendix 7.5-165 Figure 8. 13C NMR (150 MHz, CDCl3) of 31
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Appendix 7.5-166 Figure 9. 1H NMR (600 MHz, CDCl3) of 33
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Appendix 7.5-167 Figure 10. 13C NMR (150 MHz, CDCl3) of 33
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Appendix 7.5-168 Figure 11. 1H NMR (500 MHz, CDCl3) of 36
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Appendix 7.5-169 Figure 12. 13C NMR (125 MHz, CDCl3) of 36
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Appendix 7.5-170 Figure 13. 1H NMR (600 MHz, CDCl3) of 37
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Appendix 7.5-171 Figure 14. 13C NMR (150 MHz, CDCl3) of 37
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Appendix 7.5-172 Figure 15. 1H NMR (600 MHz, CDCl3) of 38
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Appendix 7.5-173 Figure 16. 13C NMR (150 MHz, CDCl3) of 38
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Appendix 7.5-174 Figure 17. 1H NMR (600 MHz, CDCl3) of 39
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Appendix 7.5-175 Figure 18. 13C NMR (150 MHz, CDCl3) of 39
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Appendix 7.5-176 Figure 19. 1H NMR (600 MHz, CDCl3) of 40
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Appendix 7.5-177 Figure 20. 13C NMR (150 MHz, CDCl3) of 40
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Appendix 7.5-178 Figure 21. 1H NMR (400 MHz, CDCl3) of 45
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Appendix 7.5-179 Figure 22. 13C NMR (150 MHz, CDCl3) of 45
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Appendix 7.5-180 Figure 23. 1H NMR (400 MHz, CDCl3) of 46
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Appendix 7.5-181 Figure 24. 13C NMR (125 MHz, CDCl3) of 46
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Appendix 7.5-182 Figure 25. 1H NMR (400 MHz, CDCl3) of 47
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Appendix 7.5-183 Figure 26. 13C NMR (125 MHz, CDCl3) of 47
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Appendix 7.5-184 Figure 27. 1H NMR (400 MHz, CDCl3) of 48
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Appendix 7.5-185 Figure 28. 13C NMR (125 MHz, CDCl3) of 48
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Appendix 7.5-186 Figure 29. 1H NMR (400 MHz, CDCl3) of 49