Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007
Wuweizidilactones A F: Novel highly oxygenated nortriterpenoids with unusual skeletons from Schisandra chinensis Sheng-Xiong Huang, Li-Bin Yang, Wei-Lie Xiao, Chun Lei, Jing-Pin Liu, Yang Lu, Zhi-Ying Weng, Li-Mei Li, Rong-Tao Li, Jun-Lin Yu, Qi-Tai Zheng, and Han-Dong Sun 1
Supporting Information Table S1. Detailed 2D NMR data of 3 (pyridine-d 5, 125 MHz) Position COSY (H? H) HMBC (H? C) ROESY (H? H) H-1 H-2ß C-2, 3, 10, 19 H-2ß, H-19a, H-19ß, H 3-29 H-2a H-2ß C-1, 3, 10 H-1 H-2ß H-1, H-2a C-1, 3 H-1 H-5 H-6a, H-6ß C-4, 7, 10, 29, 30 H-6a, H 3-30 H-6a H-5, H-7 C-4, 5, 7, 8 H-5, H 3-30 H-6ß H-5 C-4, 5, 8, 10 H 3-29 H-7 H-6a, H-8(weak) C-5, 6, 8, 14 and OAc H-6, H-8, H-15, H 3-18 H-8 H-7 (weak) C-9, 11, 14, 19 H-7, H 3-18 H-11a H-11ß, H 2-12 C-12, 13 H-19a H-11ß H-11a, H 2-12 C-8, 9, 12, 13, 19 H-12a H-11a, H-11ß, H-12ß C-9, 11 H-17 H-12ß H-11a, H-11ß, H-12a- C-9, 11, 13, 14 H-15 H 2-16 C-13, 17, 18 H-7, H 2-16, H 3-18 H 2-16 H-15, H-17 C-13, 14, 15, 17 H-15, 17, H 3-18, H 3-21 H-17 H-16, H-20 C-13, 14, 20, 22 H-12a, H 2-16, H-20 H 3-18 C-8, 13, 14, 15 H-7, H-8, H-15, H 2-16, H-22 H-19a H-19ß C-1, 5, 8, 9, 10 H-1, H-11a H-19ß H-19a C-1, 5, 8, 9, 10 H-1, H-20 H-17, H 3-21, H-22 C-17, 21, 22, 23 H-17, H 3-21, H-23 H 3-21 H-20 C-17, 20, 22 H 2-16, H-20, H-22, H-24 H-22 H-20, H-23 C-20, 21, 23, 24 H 3-18, H-20, H 3-21, H-24 H-23 H-22, H-24 H-20, H-24 H-24 H-23, H 3-27 C-23, 25, 27 H-22, H 3-27 H 3-27 H-24 C-24, 25, 26 H-24 2
H 3-29 C-4, 5, 30 H-1, H-6ß H 3-30 C-4, 5, 29 H-5, H-6a 3
Coordinates and optimized energies of computations (method: B3LYP/6-31G) Wuweizidilactone C (3): Standard orientation: --------------------------------------------------------------------- Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z --------------------------------------------------------------------- 1 6 0-2.485123-0.591524-1.822912 2 6 0-1.565651 0.561050-1.370980 3 6 0-0.503756 0.133468-0.320997 4 6 0-1.058861-0.127450 1.117764 5 6 0-2.135961-1.246111 1.139313 6 1 0-0.210100-0.871224-0.650035 7 8 0-1.612888 1.010782 1.757024 8 1 0-1.252789 1.809984 1.332303 9 8 0-2.410803 1.630032-0.879150 10 6 0 0.860241 0.938636-0.450235 11 6 0 1.873673 0.738995 0.757226 12 6 0 1.189699 0.441089 2.094761 13 6 0 0.121946-0.637574 1.985563 14 6 0 0.775050 2.481670-0.552402 15 6 0 2.216862 2.957601-0.306364 16 6 0 2.736185 2.038771 0.823561 17 8 0 2.790134-0.345972 0.502756 18 6 0 4.097180 0.124893 0.190523 19 6 0 4.208596 1.545187 0.793462 20 6 0 5.076516-0.918996 0.754119 21 8 0 4.908633-2.148952 0.024898 22 6 0 6.107787-2.538527-0.516659 23 6 0 7.146482-1.546779-0.115271 24 6 0 6.543026-0.610644 0.625710 4
25 8 0 6.233908-3.532921-1.188060 26 6 0 8.572101-1.714344-0.525829 27 6 0 5.198748 2.474850 0.082968 28 1 0 2.553333 2.542131 1.776707 29 6 0-2.454312 2.806943-1.535646 30 6 0-3.466456 3.724717-0.891479 31 8 0-1.785685 3.079507-2.513336 32 6 0-3.547191-1.044100 0.566773 33 6 0-4.453468-2.279778 0.876670 34 8 0-5.337976-2.393858-0.226876 35 6 0-4.622763-2.029409-1.426219 36 8 0-4.215226 0.054763 1.247520 37 6 0-5.179403-0.360479 2.110498 38 6 0-5.234255-1.884178 2.115946 39 8 0-5.849567 0.407753 2.751005 40 6 0-3.837975-3.250685-1.934601 41 6 0-5.677246-1.609850-2.449084 42 1 0-3.863273-3.197425 1.006499 43 6 0-3.731128-0.830385-0.961846 44 1 0-4.349325 0.067174-1.038131 45 8 0-0.088511 2.976041 0.492580 46 1 0-0.162000 3.938185 0.398466 47 6 0 1.521284 0.429551-1.758822 48 1 0-4.475857 3.409259-1.179440 49 1 0-3.305980 4.748150-1.234527 50 1 0-3.408159 3.658584 0.197932 51 1 0-5.204696-1.249066-3.369676 52 1 0-6.304765-0.811886-2.040275 53 1 0-6.322063-2.456704-2.706697 54 1 0-3.361444-3.051815-2.900288 5
55 1 0-4.529463-4.089556-2.062725 56 1 0-3.055867-3.564829-1.234109 57 1 0 6.226905 2.108276 0.159378 58 1 0 5.174776 3.477969 0.523218 59 1 0 4.971396 2.572358-0.983852 60 1 0 2.456821 0.943385-1.990667 61 1 0 1.750091-0.634749-1.674714 62 1 0 0.862495 0.579517-2.619483 63 1 0 8.963475-2.674013-0.168556 64 1 0 8.656841-1.732866-1.618715 65 1 0 9.202587-0.909722-0.137283 66 1 0-4.765776-2.252199 3.036297 67 1 0-6.267900-2.235626 2.095958 68 1 0 2.245262 4.018237-0.029797 69 1 0 2.796900 2.863880-1.228786 70 1 0 7.012999 0.239456 1.106806 71 1 0 4.789650-1.111459 1.796552 72 1 0 4.529861 1.437239 1.839515 73 1 0 4.244629 0.156694-0.900751 74 1 0 0.382170 2.804758-1.521751 75 1 0 0.548650-1.560580 1.571105 76 1 0-0.268302-0.870953 2.982860 77 1 0 0.713790 1.351629 2.470379 78 1 0 1.968665 0.155024 2.811622 79 1 0-1.056658 0.944775-2.255381 80 1 0-2.274723-1.501735 2.198182 81 1 0-1.712512-2.143380 0.667790 82 1 0-2.832702-0.367470-2.840235 83 1 0-1.874039-1.496473-1.905654 --------------------------------------------------------------------- 6
The complete ref.10 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr. T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. Petersson, A. H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratemann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuk, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03 User s Reference Gaussian Inc. 2003, Carnegie, PA. 15106, USA. 7
8
9 ESIMS spectra of wuweizidilactone A (1)
10 HRESIMS spectra of wuweizidilactone A (1)
1 H NMR spectrum of wuweizidilactone A (1) 7. 1420 7. 1405 5. 8857 5. 8717 5. 7470 5. 7302 4. 9755 4. 9117 4. 3022 4. 2920 4. 0690 4. 0654 3. 9678 3. 9605 3. 9480 3. 9407 3. 8270 3. 4148 3. 4112 3. 3884 3. 3848 3. 3319 3. 0525 3. 0415 2. 8464 2. 7951 2. 7592 2. 7152 2. 6888 2. 5626 2. 5318 2. 2685 2. 2384 2. 1072 1. 9942 1. 9927 1. 9583 1. 9421 1. 9297 1. 9135 1. 7551 1. 6598 1. 6429 1. 6312 1. 6143 1. 2139 1. 0643 0. 8596 0. 8464 9. 5 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 (ppm) 11
13 C and DEPT NMR spectra of wuweizidilactone A (1) 12
202. 6943 174. 6804 173. 9436 166. 1389 146. 2945 140. 2639 131. 2073 127. 5375 97. 6493 94. 0653 85. 6382 84. 0858 81. 8181 81. 5177 79. 1712 72. 5040 69. 5352 56. 6585 54. 5553 54. 0045 46. 2070 45. 2054 41. 4855 37. 7942 35. 2475 30. 5403 30. 3472 27. 9507 26. 3053 21. 7341 20. 8542 15. 9038 11. 8763 10. 6888 200 190 180 170 160 150 140 130 120 110 (ppm) 100 90 80 70 60 50 40 30 20 10 13
HSQC spectrum of wuweizidilactone A (1) ( ppm ) 40 80 120 160 ( ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 14
15 HMBC spectrum of wuweizidilactone A (1)
( ppm ) 40 80 120 160 200 ( ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 16
17 HRESIMS spectra of wuweizidilactone B (2)
1 H NMR spectrum of wuweizidilactone B (2) 7. 1768 5. 8152 5. 7981 5. 6607 5. 6407 5. 4426 5. 0193 4. 9753 4. 2492 4. 2365 3. 9632 3. 9549 3. 9383 3. 9300 3. 7789 3. 6640 3. 0323 3. 0196 2. 9003 2. 7796 2. 7444 2. 7346 2. 6886 2. 6652 2. 5410 2. 5254 2. 3181 2. 3146 2. 2090 2. 2017 2. 0619 2. 0457 1. 7817 1. 6263 1. 5896 1. 1990 0. 9951 0. 8763 0. 8597 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 (ppm) 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 18
13 C and DEPT NMR spectra of wuweizidilactone B (2) 174. 8664 174. 1009 170. 8460 166. 3821 146. 7237 139. 3697 130. 8782 127. 9667 98. 1858 90. 7173 84. 9371 84. 1860 82. 0399 81. 3817 75. 2224 70. 4366 70. 1504 69. 7355 55. 1849 53. 8471 46. 1926 46. 0782 43. 5958 41. 4855 36. 5566 35. 6266 30. 9338 28. 3513 26. 9062 22. 0918 21. 4122 21. 0831 15. 8895 11. 6545 10. 7317 180 170 160 150 140 130 120 110 100 (ppm) 90 80 70 60 50 40 30 20 10 19
HSQC spectrum of wuweizidilactone B (2) (ppm ) 40 80 120 160 (ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 20
HMBC spectrum of wuweizidilactone B (2) ( ppm ) 40 80 120 160 ( ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 21
ROESY spectrum of wuweizidilactone B (2) (ppm ) 2. 0 4. 0 6. 0 8. 0 (ppm ) 8. 0 6. 0 4. 0 2. 0 22
23 FABMS spectra of wuweizidilactone C (3)
24 HRESIMS spectra of wuweizidilactone C (3)
25 1 H NMR spectrum of wuweizidilactone C (3)
7. 2480 6. 0490 5. 9190 5. 8904 5. 8745 5. 0105 4. 3295 4. 3197 3. 9664 3. 9621 3. 8261 3. 8181 3. 8072 3. 7998 3. 0200 2. 8791 2. 8589 2. 8064 2. 7698 2. 6338 2. 6283 2. 6063 2. 5593 2. 5441 2. 3561 2. 3488 2. 3403 2. 3354 2. 3268 2. 3195 2. 1688 2. 1181 1. 9906 1. 9296 1. 8015 1. 6025 1. 5763 1. 4213 1. 2974 1. 1687 1. 0637 0. 9264 0. 9124 OAc H-19 Á Me-29 Me-30 Me-18 Me-27 H-24 OH-9 OH-15 H-7 H-23 H-1 H-15 H-22 H-12 Á H-8 H-5 H-11 Á H-17 H-20 H-6 Á H-19 Â H-2 Á H 2-16 H-11 Â H-2 Â H-6 Â Me-21 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 4. 5 (ppm) 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 13 C and DEPT NMR spectra of wuweizidilactone C (3) 26
174. 9688 174. 3818 170. 7024 146. 8220 130. 7156 99. 1900 94. 9236 88. 9392 84. 6298 82. 3821 82. 0099 79. 4042 72. 4319 70. 1413 58. 3585 55. 2947 52. 4028 52. 2596 46. 9051 39. 5320 36. 1532 35. 9384 35. 3371 33. 3757 31. 6291 29. 0521 24. 5566 22. 9961 20. 9488 12. 8312 10. 8268 C-26 C-3 OAc C-24 C-23 C-1 C-22 C-15 C-25 C-10 C-13 C-4 C-9 C-7 C-8 C-5 C-17 C-19 C-11 C-14 C-2 C-20 C-12 C-6 C-18 C-21 C-16 C-30 C-29 OAc C-27 180 170 160 150 140 130 120 110 100 (ppm) 90 80 70 60 50 40 30 20 10 HSQC NMR spectrum of wuweizidilactone C (3) 27
( ppm ) 20 40 60 80 100 120 140 ( ppm ) 8. 0 6. 0 4. 0 2. 0 28
1 H- 1 H COSY NMR spectrum of wuweizidilactone C (3) (ppm ) 2. 0 4. 0 6. 0 8. 0 (ppm ) 8. 0 6. 0 4. 0 2. 0 HMBC NMR spectrum of wuweizidilactone C (3) 29
(ppm ) 40 80 120 160 (ppm ) 8. 0 6. 0 4. 0 2. 0 ROESY NMR spectrum of wuweizidilactone C (3) 30
( ppm ) 2. 0 4. 0 6. 0 8. 0 ( ppm ) 8. 0 6. 0 4. 0 2. 0 0. 0 1 H NMR spectrum of wuweizidilactone D (4) 31
7. 2796 6. 8958 6. 8851 4. 2440 4. 2333 4. 0716 4. 0653 3. 8633 3. 8544 3. 8393 3. 8305 2. 8740 2. 7205 2. 6764 2. 5959 2. 5877 2. 2189 2. 1233 2. 0125 1. 9257 1. 7627 1. 5236 1. 4896 1. 4802 1. 4210 1. 2801 1. 1378 1. 0523 0. 9409 0. 9232 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 (ppm) 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 32
13 C and DEPT NMR spectra of wuweizidilactone D (4) 175. 7750 174. 4873 147. 1816 130. 5063 99. 7382 93. 4000 87. 8845 85. 0516 82. 2545 81. 8325 78. 8351 70. 1934 58. 7761 57. 5599 55. 1563 53. 5753 47. 7164 38. 2449 37. 0073 35. 9844 35. 8127 32. 9941 29. 9824 29. 0381 25. 4469 24. 0234 23. 6371 12. 5417 10. 8534 180 170 160 150 140 130 120 110 100 (ppm) 90 80 70 60 50 40 30 20 10 33
34 HSQC NMR spectrum of wuweizidilactone D (4)
(ppm ) 40 80 120 (ppm ) 8. 0 6. 0 4. 0 2. 0 0. 0 160 HMBC NMR spectrum of wuweizidilactone D (4) 35
(ppm ) 40 80 120 160 (ppm ) 8. 0 6. 0 4. 0 2. 0 0. 0 1 H NMR spectrum of wuweizidilactone E (5) 36
7. 2725 5. 1222 5. 1156 5. 0547 5. 0510 4. 2201 4. 2113 4. 1504 3. 7955 3. 7837 2. 9212 2. 9117 2. 8853 2. 8765 2. 7144 2. 6792 2. 5736 2. 5663 2. 5465 2. 5391 2. 5318 2. 5135 2. 5039 2. 4922 2. 3895 2. 3844 2. 0874 2. 0756 1. 9861 1. 9260 1. 8930 1. 8849 1. 8783 1. 8725 1. 8615 1. 8512 1. 8050 1. 7793 1. 7742 1. 7529 1. 7287 1. 6187 1. 5688 1. 5527 1. 5410 1. 5241 1. 4390 1. 4200 1. 4126 1. 3591 1. 3385 1. 3334 1. 3041 1. 2403 1. 2234 1. 1097 1. 0378 0. 9124 0. 9007 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 (ppm) 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 13 C and DEPT NMR spectra of wuweizidilactone E (5) 37
175. 4612 174. 3639 169. 8903 147. 0020 130. 5427 99. 9594 93. 0802 87. 2140 85. 1319 82. 1355 81. 8823 81. 4321 70. 5577 58. 6423 57. 8123 53. 5075 53. 0996 48. 6401 37. 9908 37. 0201 35. 9932 34. 6567 30. 7740 30. 0003 29. 4235 25. 5267 24. 2888 23. 6557 21. 5174 12. 0920 10. 8118 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 (ppm) HSQC NMR spectrum of wuweizidilactone E (5) 38
(ppm ) 40 80 120 160 (ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 HMBC NMR spectrum of wuweizidilactone E (5) 39
(ppm ) 40 80 120 160 (ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 ROESY NMR spectrum of wuweizidilactone E (5) 40
(ppm ) 2. 0 4. 0 6. 0 8. 0 (ppm ) 8. 0 6. 0 4. 0 2. 0 1 H NMR spectrum of wuweizidilactone F (6) 41
7. 2599 5. 1226 5. 1163 4. 6562 4. 3686 4. 1612 3. 7974 3. 7854 3. 7799 2. 7176 2. 6858 2. 6564 2. 6509 2. 6302 2. 6238 2. 5174 2. 5055 2. 4896 2. 3505 2. 3458 2. 1153 1. 9946 1. 9199 1. 8301 1. 8222 1. 7983 1. 7157 1. 6863 1. 5600 1. 4464 1. 4225 1. 3701 1. 2533 1. 1556 1. 0443 0. 9109 0. 8997 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 (ppm) 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 13 C and DEPT NMR spectra of wuweizidilactone F (6) 42
177. 2415 174. 4802 169. 9662 147. 1745 130. 4062 100. 5967 93. 0066 87. 3337 87. 0046 85. 8314 81. 9398 81. 1815 73. 7631 70. 6012 58. 6688 57. 5671 53. 4108 52. 9888 49. 7553 38. 0017 35. 9343 34. 6610 30. 7407 30. 1255 29. 3171 25. 7904 24. 2738 24. 0663 21. 5911 12. 0481 10. 8749 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 (ppm) HSQC NMR spectrum of wuweizidilactone F (6) 43
(ppm ) 40 80 120 160 (ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 HMBC NMR spectrum of wuweizidilactone F (6) 44
( ppm ) 40 80 120 160 ( ppm ) 10. 0 8. 0 6. 0 4. 0 2. 0 0. 0 ROESY NMR spectrum of wuweizidilactone F (6) 45
(ppm ) 2. 0 4. 0 6. 0 8. 0 (ppm ) 8. 0 6. 0 4. 0 2. 0 0. 0 46
47 1 H NMR spectrum of micrandilactone B (7)
8. 7002 7. 5753 7. 2125 5. 1410 4. 2810 4. 0018 3. 5736 3. 5697 3. 3609 3. 0133 2. 9688 2. 7434 2. 6989 2. 5136 2. 4814 2. 2384 2. 1988 2. 1685 2. 0819 1. 8961 1. 8658 1. 8204 1. 7411 1. 7118 1. 4835 1. 3725 1. 3422 1. 2532 1. 1178 0. 9359 9. 5 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 ( ppm) 1 H NMR spectrum of (R)-MTPA ester of 7 48
8. 7105 8. 0703 7. 7122 7. 5546 7. 4275 7. 3712 7. 3241 7. 1882 5. 5213 5. 3833 4. 2796 4. 2682 3. 8228 3. 6011 3. 3743 2. 9655 2. 9536 2. 7655 2. 7211 2. 6958 2. 5325 2. 5087 2. 2173 2. 1822 2. 1315 2. 0891 1. 9786 1. 9501 1. 8396 1. 7879 1. 7243 1. 6473 1. 6153 1. 5616 1. 5295 1. 4179 1. 2510 1. 1146 1. 0882 1. 0712 0. 9374 9. 5 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 (ppm) 1 H NMR spectrum of (S)-MTPA ester of 7 49
8. 7100 8. 0682 8. 0491 7. 5592 7. 4440 7. 4264 7. 4084 7. 2234 5. 6112 5. 3626 4. 2873 4. 2765 3. 8207 3. 5567 3. 3877 2. 9717 2. 9609 2. 7671 2. 7227 2. 6999 2. 5413 2. 5325 2. 5082 2. 4989 2. 2199 2. 0969 1. 9827 1. 8757 1. 8659 1. 7119 1. 5791 1. 4210 1. 2686 1. 2520 1. 1208 0. 9518 9. 5 9. 0 8. 5 8. 0 7. 5 7. 0 6. 5 6. 0 5. 5 5. 0 4. 5 4. 0 3. 5 3. 0 2. 5 2. 0 1. 5 1. 0 0. 5 (ppm) COSY spectrum of (R)-MTPA ester of 7 50
(ppm ) 2. 0 4. 0 6. 0 8. 0 (ppm ) 8. 0 6. 0 4. 0 2. 0 COSY spectrum of (S)-MTPA ester of 7 51
( ppm ) 2. 0 4. 0 6. 0 8. 0 ( ppm ) 8. 0 6. 0 4. 0 2. 0 52