Supporting Information. Research Center for Marine Drugs, Department of Pharmacy, State Key Laboratory
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1 Supporting Information Dysiherbols A C and Dysideanone E, Cytotoxic and NF-κB Inhibitory Tetracyclic Meroterpenes from a Dysidea sp. Marine Sponge Wei-Hua Jiao,, Guo-Hua Shi,, Ting-Ting Xu,, Guo-Dong Chen, Bin-Bin Gu, Zhuo Wang, Shuang Peng,, Shu-Ping Wang, Jia Li, Bing-Nan Han, Wei Zhang, and Hou-Wen Lin*, Research Center for Marine Drugs, Department of Pharmacy, State Key Laboratory of Oncogenes and Related Genes, Ren Ji Hospital, School of Medicine, Shanghai Jiao Tong University, Shanghai 2007, People s Republic of China Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 50632, People s Republic of China Center for Marine Bioproducts Development, Flingers University, Adelaide 500, Australia National Center for Drug Screening, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, 2003, People s Republic of China
2 Contents A Photo of a Dysidea sp. Marine Sponge (No. XD0608) Experimental Section Figure S. H NMR Spectrum of Dysiherbol A () in CDCl 3. Figure S2. C NMR Spectrum of Dysiherbol A () in CDCl 3. Figure S3. DEPT5 Spectrum of Dysiherbol A () in CDCl 3. Figure S4. H- H COSY Spectrum of Dysiherbol A () in CDCl 3. Figure S5. HSQC Spectrum of Dysiherbol A () in CDCl 3. Figure S6. HMBC Spectrum of Dysiherbol A () in CDCl 3. Figure S7. NOESY Spectrum of Dysiherbol A () in CDCl 3. Figure S8. HRESIMS of Dysiherbol A (). Figure S9. ECD spectrum of Dysiherbol A () in MeOH. Figure S0. UV spectrum of Dysiherbol A () in MeOH. Figure S. IR spectrum of Dysiherbol A (). Figure S. H NMR Spectrum of Dysiherbol B (2) in Pyr-d 5. Figure S. C NMR Spectrum of Dysiherbol B (2) in Pyr-d 5. Figure S. DEPT5 Spectrum of Dysiherbol B (2) in Pyr-d 5. Figure S. H- H COSY Spectrum of Dysiherbol B (2) in Pyr-d 5. Figure S6. HSQC Spectrum of Dysiherbol B (2) in Pyr-d 5. Figure S7. HMBC Spectrum of Dysiherbol B (2) in Pyr-d 5. Figure S8. NOESY Spectrum of Dysiherbol B (2) in Pyr-d 5. Figure S9. HRESIMS of Dysiherbol B (2). Figure S20. ECD spectrum of Dysiherbol B (2). Figure S. UV spectrum of Dysiherbol B (2) in MeOH. Figure S22. IR spectrum of Dysiherbol B (2). 2
3 Figure S23. H NMR Spectrum of Dysiherbol C (3) in CDCl 3. Figure S24. C NMR Spectrum of Dysiherbol C (3) in CDCl 3. Figure S25. DEPT5 Spectrum of Dysiherbol C (3) in CDCl 3. Figure S26. H- H COSY Spectrum of Dysiherbol C (3) in CDCl 3. Figure S27. HSQC Spectrum of Dysiherbol C (3) in CDCl 3. Figure S28. HMBC Spectrum of Dysiherbol C (3) in CDCl 3. Figure S29. NOESY Spectrum of Dysiherbol C (3) in CDCl 3. Figure S30. HRESIMS of Dysiherbol C (3). Figure S3. ECD spectrum of Dysiherbol C (3). Figure S22. UV spectrum of Dysiherbol C (3) in MeOH. Figure S33. IR spectrum of Dysiherbol C (3). Figure S34. H NMR Spectrum of Dysideanone E (4) in CDCl 3. Figure S35. C NMR Spectrum of Dysideanone E (4) in CDCl 3. Figure S36. DEPT5 Spectrum of Dysideanone E (4) in CDCl 3. Figure S37. H- H COSY Spectrum of Dysideanone E (4) in CDCl 3. Figure S38. HSQC Spectrum of Dysideanone E (4) in CDCl 3. Figure S39. HMBC Spectrum of Dysideanone E (4) in CDCl 3. Figure S40. NOESY Spectrum of Dysideanone E (4) in CDCl 3. Figure S4. HRESIMS of Dysideanone E (4). Figure S42. ECD spectrum of Dysideanone E (4). Figure S43. Experimental and calculated ECD spectra of 4. Figure S44. UV spectrum of Dysideanone E (4) in MeOH. Figure S45. IR spectrum of Dysideanone E (4). Table S. Crystallographic Table for Dysideanone E (4). 3
4 A Photo of a Dysidea sp. Marine Sponge (No. XD0608) 4
5 Figure S. H NMR Spectrum of Dysiherbol A () in CDCl 3. 5
6 Figure S2. C NMR Spectrum of Dysiherbol A () in CDCl 3. 6
7 Figure S3. DEPT5 Spectrum of Dysiherbol A () in CDCl 3. 7
8 Figure S4. H- H COSY Spectrum of Dysiherbol A () in CDCl 3. 8
9 Figure S5. HSQC Spectrum of Dysiherbol A () in CDCl 3. 9
10 Figure S6. HMBC Spectrum of Dysiherbol A () in CDCl 3. 0
11 7 OH Dysiherbol A () Figure S7. NOESY Spectrum of Dysiherbol A () in CDCl 3.
12 7 OH Dysiherbol A () Figure S8. HRESIMS of Dysiherbol A ().
13 7 OH Dysiherbol A () Figure S9. ECD Spectrum of Dysiherbol A ().
14 7 OH Dysiherbol A () Figure S0. UV Spectrum of Dysiherbol A () in MeOH.
15 7 OH Dysiherbol A () Figure S. IR Spectrum of Dysiherbol A ().
16 7 OH Dysiherbol B (2) Figure S. H NMR Spectrum of Dysiherbol B (2) in Pyr-d 5. 6
17 7 OH Dysiherbol B (2) Figure S. C NMR Spectrum of Dysiherbol B (2) in Pyr-d 5. 7
18 7 OH Dysiherbol B (2) Figure S. DEPT5 Spectrum of Dysiherbol B (2) in Pyr-d 5. 8
19 7 OH Dysiherbol B (2) Figure S. H- H COSY Spectrum of Dysiherbol B (2) in Pyr-d 5. 9
20 7 OH Dysiherbol B (2) Figure S6. HSQC Spectrum of Dysiherbol B (2) in Pyr-d 5. 20
21 7 OH Dysiherbol B (2) Figure S7. HMBC Spectrum of Dysiherbol B (2) in Pyr-d 5.
22 7 OH Dysiherbol B (2) Figure S8. NOESY Spectrum of Dysiherbol B (2) in Pyr-d 5. 22
23 7 OH Dysiherbol B (2) Figure S9. HRESIMS of Dysiherbol B (2). 23
24 7 OH Dysiherbol B (2) Figure S20. ECD Spectrum of Dysiherbol B (2). 24
25 7 OH Dysiherbol B (2) Figure S. UV Spectrum of Dysiherbol B (2) in MeOH. 25
26 7 OH Dysiherbol B (2) Figure S22. IR Spectrum of Dysiherbol B (2). 26
27 Figure S23. H NMR Spectrum of Dysiherbol C (3) in CDCl 3. 27
28 Figure S24. C NMR Spectrum of Dysiherbol C (3) in CDCl 3. 28
29 Figure S25. DEPT5 Spectrum of Dysiherbol C (3) in CDCl 3. 29
30 Figure S26. H- H COSY Spectrum of Dysiherbol C (3) in CDCl 3. 30
31 Figure S27. HSQC Spectrum of Dysiherbol C (3) in CDCl 3. 3
32 Figure S28. HMBC Spectrum of Dysiherbol C (3) in CDCl 3. 32
33 Figure. S29. NOESY Spectrum of Dysiherbol C (3) in CDCl 3. 33
34 7 OH 20 6 O Dysiherbol C (3) Figure S30. HRESIMS of Dysiherbol C (3). 34
35 7 OH 20 6 O Dysiherbol C (3) Figure S3. ECD Spectrum of Dysiherbol C (3) in MeOH. 35
36 7 OH 20 6 O Dysiherbol C (3) Figure S32. UV Spectrum of Dysiherbol C (3) in MeOH. 36
37 7 OH 20 6 O Dysiherbol C (3) Figure S33. IR Spectrum of Dysiherbol C (3). 37
38 20 O H 4 6 H Dysideanone E (4) Figure S34. H NMR Spectrum of Dysideanone E (4) in CDCl 3. 38
39 20 O H 4 6 H Dysideanone E (4) Figure S35. C NMR Spectrum of Dysideanone E (4) in CDCl 3. 39
40 20 O H 4 6 H Dysideanone E (4) Figure S36. DEPT5 Spectrum of Dysideanone E (4) in CDCl 3. 40
41 20 O H 4 6 H Dysideanone E (4) Figure S37. H- H COSY Spectrum of Dysideanone E (4) in CDCl 3. 4
42 20 O H 4 6 H Dysideanone E (4) Figure S38. HSQC Spectrum of Dysideanone E (4) in CDCl 3. 42
43 20 O H 4 6 H Dysideanone E (4) Figure S39. HMBC Spectrum of Dysideanone E (4) in CDCl 3. 43
44 20 O H 4 6 H Dysideanone E (4) Figure S40. NOESY Spectrum of Dysideanone E (4) in CDCl 3. 44
45 20 O H 4 6 H Dysideanone E (4) Figure S4. HRESIMS of Dysideanone E (4). 45
46 20 O H 4 6 H Dysideanone E (4) Figure S42. ECD Spectrum of Dysideanone E (4). 46
47 Figure S43. Experimental and calculated ECD spectra of 4. 47
48 20 O H 4 6 H Dysideanone E (4) Figure S44. UV Spectrum of Dysideanone E (4) in MeOH. 48
49 20 O H 4 6 H Dysideanone E (4) Figure S45. IR Spectrum of Dysideanone E (4). 49
50 Table S. Crystallographic Table for Dysideanone E (4). Table. Crystal data and structure refinement for cu_dm635_0m. Identification code cu_dm635_0m Empirical formula C H28 O2 Formula weight 3.43 Temperature 0 K Wavelength.5478 Å Crystal system Monoclinic Space group P Unit cell dimensions a = 0.40(3) Å α= 90. b = 6.592(2) Å β= (2). c =.5869(3) Å γ = 90. Volume (4) Å 3 Z 2 Density (calculated).220 Mg/m 3 Absorption coefficient 0.59 mm - F(000) 340 Crystal size 0. x 0.08 x 0.03 mm 3 Theta range for data collection to Index ranges -<=h<=, -7<=k<=7, -<=l<= Reflections collected 640 Independent reflections 2646 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 2646 / / 2 Goodness-of-fit on F Final R indices [I>2sigma(I)] R = 0.044, wr2 = 0.95 R indices (all data) R = , wr2 = 0.78 Absolute structure parameter 0.07() Extinction coefficient n/a Largest diff. peak and hole 0.37 and e.å -3 50
51 Table 2. Atomic coordinates ( x 0 4 ) and equivalent isotropic displacement parameters (Å 2 x 0 3 ) for cu_dm635_0m. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) O() 3945(2) 876(3) 73() 22() O(2) 4097(2) 607(4) 3449(2) 30() C() 3492(2) 56(4) 75(2) 9() C(2) 4625(2) 4934(5) 8379(2) 23() C(3) 4303(3) 3589(5) 939(2) 26() C(4) 3066(3) 4267(4) 9750(2) 24() C(5) 900(3) 48(4) 8924(2) () C(6) 686(3) 4993(5) 9395(2) 24() C(7) -463(3) 58(5) 8563(2) 27() C(8) -2(2) 6629(5) 765(2) 23() C(9) 050(2) 5892(4) 706(2) 20() C(0) 220(2) 5624(4) 7983(2) 8() C() 3025(3) 4858(6) 0755(2) 3() C() 7(3) 890(5) 868(2) 27() C() -60(3) 6962(6) 6882(2) 33() C() 740(3) 3945(5) 6425(2) 26() C() 46(2) 7608(5) 6348(2) 22() C(6) 2688(2) 702(4) 5885(2) 20() C(7) 389(2) 688(4) 67(2) 20() C(8) 5060(2) 6446(4) 6230(2) () C(9) 59(3) 698(5) 587(2) 23() C(20) 407(3) 6329(5) 44(2) 23() C() 2788(3) 6806(5) 4845(2) 23() 5
52 Table 3. Bond lengths [Å] and angles [ ] for cu_dm635_0m. O()-H() O()-C(7).439(3) O(2)-C(20).236(3) C()-H(A).0000 C()-C(2).547(3) C()-C(0).543(3) C()-C(7).567(4) C(2)-H(2A) C(2)-H(2B) C(2)-C(3).53(4) C(3)-H(3A) C(3)-H(3B) C(3)-C(4).502(4) C(4)-C(5).533(3) C(4)-C().326(4) C(5)-C(6).532(4) C(5)-C(0).564(3) C(5)-C().55(4) C(6)-H(6A) C(6)-H(6B) C(6)-C(7).53(4) C(7)-H(7A) C(7)-H(7B) C(7)-C(8).526(4) C(8)-H(8).0000 C(8)-C(9).550(3) C(8)-C().538(3) C(9)-C(0).57(3) C(9)-C().55(4) C(9)-C().548(4) C(0)-H(0).0000 C()-H(A) C()-H(B) C()-H(A) C()-H(B) C()-H(C)
53 C()-H(A) C()-H(B) C()-H(C) C()-H(A) C()-H(B) C()-H(C) C()-H(A) C()-H(B) C()-C(6).497(3) C(6)-C(7).56(3) C(6)-C().335(4) C(7)-C(8).499(4) C(8)-H(8) C(8)-C(9).334(4) C(9)-H(9) C(9)-C(20).475(3) C(20)-C().462(4) C()-H() C(7)-O()-H() 09.5 C(2)-C()-H(A) 08.5 C(2)-C()-C(7) 08.9(2) C(0)-C()-H(A) 08.5 C(0)-C()-C(2).48(9) C(0)-C()-C(7) 0.0(2) C(7)-C()-H(A) 08.5 C()-C(2)-H(2A) 08.9 C()-C(2)-H(2B) 08.9 H(2A)-C(2)-H(2B) 07.7 C(3)-C(2)-C().3(2) C(3)-C(2)-H(2A) 08.9 C(3)-C(2)-H(2B) 08.9 C(2)-C(3)-H(3A) 09.5 C(2)-C(3)-H(3B) 09.5 H(3A)-C(3)-H(3B) 08.0 C(4)-C(3)-C(2) 0.9(2) C(4)-C(3)-H(3A) 09.5 C(4)-C(3)-H(3B)
54 C(3)-C(4)-C(5).5(2) C()-C(4)-C(3).6(2) C()-C(4)-C(5) 4.9(3) C(4)-C(5)-C(0) 07.(2) C(4)-C(5)-C() 06.3(2) C(6)-C(5)-C(4) 0.9(2) C(6)-C(5)-C(0) 07.9(2) C(6)-C(5)-C() 09.7(2) C()-C(5)-C(0).8(2) C(5)-C(6)-H(6A) 09.0 C(5)-C(6)-H(6B) 09.0 H(6A)-C(6)-H(6B) 07.8 C(7)-C(6)-C(5).0(2) C(7)-C(6)-H(6A) 09.0 C(7)-C(6)-H(6B) 09.0 C(6)-C(7)-H(7A) 09.3 C(6)-C(7)-H(7B) 09.3 H(7A)-C(7)-H(7B) 07.9 C(8)-C(7)-C(6).8(2) C(8)-C(7)-H(7A) 09.3 C(8)-C(7)-H(7B) 09.3 C(7)-C(8)-H(8) 06.6 C(7)-C(8)-C(9).0(2) C(7)-C(8)-C() 0.2(2) C(9)-C(8)-H(8) 06.6 C()-C(8)-H(8) 06.6 C()-C(8)-C(9).4(2) C(8)-C(9)-C(0) 08.64(9) C(8)-C(9)-C().0(2) C()-C(9)-C(0).2(2) C()-C(9)-C(8) 08.3(2) C()-C(9)-C(0) 06.75(9) C()-C(9)-C() 07.7(2) C()-C(0)-C(5).8(2) C()-C(0)-C(9).88(8) C()-C(0)-H(0) 04.9 C(5)-C(0)-C(9).3(2) C(5)-C(0)-H(0)
55 C(9)-C(0)-H(0) 04.9 C(4)-C()-H(A) 0.0 C(4)-C()-H(B) 0.0 H(A)-C()-H(B) 0.0 C(5)-C()-H(A) 09.5 C(5)-C()-H(B) 09.5 C(5)-C()-H(C) 09.5 H(A)-C()-H(B) 09.5 H(A)-C()-H(C) 09.5 H(B)-C()-H(C) 09.5 C(8)-C()-H(A) 09.5 C(8)-C()-H(B) 09.5 C(8)-C()-H(C) 09.5 H(A)-C()-H(B) 09.5 H(A)-C()-H(C) 09.5 H(B)-C()-H(C) 09.5 C(9)-C()-H(A) 09.5 C(9)-C()-H(B) 09.5 C(9)-C()-H(C) 09.5 H(A)-C()-H(B) 09.5 H(A)-C()-H(C) 09.5 H(B)-C()-H(C) 09.5 C(9)-C()-H(A) 09.4 C(9)-C()-H(B) 09.4 H(A)-C()-H(B) 08.0 C(6)-C()-C(9).2(2) C(6)-C()-H(A) 09.4 C(6)-C()-H(B) 09.4 C()-C(6)-C(7).5(2) C()-C(6)-C() 3.5(2) C()-C(6)-C(7) 2.9(2) O()-C(7)-C() 07.8(9) O()-C(7)-C(6) 08.2(2) O()-C(7)-C(8) 09.3(2) C(6)-C(7)-C() 08.2(2) C(8)-C(7)-C().3(2) C(8)-C(7)-C(6).5(2) C(7)-C(8)-H(8)
56 C(9)-C(8)-C(7) 4.(2) C(9)-C(8)-H(8) 7.9 C(8)-C(9)-H(9) 9.4 C(8)-C(9)-C(20).3(2) C(20)-C(9)-H(9) 9.4 O(2)-C(20)-C(9).7(2) O(2)-C(20)-C().6(2) C()-C(20)-C(9) 6.7(2) C(6)-C()-C(20) 2.3(2) C(6)-C()-H() 8.9 C(20)-C()-H() 8.9 Symmetry transformations used to generate equivalent atoms: 56
57 Table 4. Anisotropic displacement parameters (Å 2 x 0 3 ) for cu_dm635_0m. The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U ] U U 22 U 33 U 23 U U O() 25() 25() 9() -5() 6() -4() O(2) 40() 35() () 0() 8() 9() C() 20() 25() () -() 2() 0() C(2) 20() 33(2) 6() 4() 2() () C(3) 28() 32(2) 9() 8() () 5() C(4) 30() 25(2) 6() 4() 5() 0() C(5) 25() 22(2) () -2() 7() -() C(6) 29() 28(2) 7() -3() 0() -3() C(7) 22() 36(2) 24() -6() 0() -4() C(8) () 29(2) 20() -5() 3() -() C(9) 8() 27() () -7() 2() () C(0) 8() 22() () -() 3() -() C() 35() 4(2) 6() 4() () -2() C() 35() 24(2) 23() 0() 9() -3() C() 8() 5(2) 3() -4() 3() 5() C() 25() 33(2) 20() -8() () -3() C() () 30(2) () -2() () 5() C(6) 20() 22() 7() () 3() 0() C(7) 9() 25() () -2() 3() () C(8) 9() 26(2) 8() 0() 2() 0() C(9) 24() 26(2) () () 7() 2() C(20) 32() 23() () 0() 4() 2() C() 26() 27() () 0() 2() 3() 57
58 Table 5. Hydrogen coordinates ( x 0 4 ) and isotropic displacement parameters (Å 2 x 0 3 ) for cu_dm635_0m. x y z U(eq) H() H(A) H(2A) H(2B) H(3A) H(3B) H(6A) H(6B) H(7A) H(7B) H(8) H(0) H(A) H(B) H(A) H(B) H(C) H(A) H(B) H(C) H(A) H(B) H(C) H(A) H(B) H(8) H(9) H()
59 Table 6. Torsion angles [ ] for cu_dm635_0m. O()-C(7)-C(8)-C(9) -2.7(3) O(2)-C(20)-C()-C(6) -79.5(3) C()-C(2)-C(3)-C(4) -5.(3) C()-C(7)-C(8)-C(9) 9.(3) C(2)-C()-C(0)-C(5) -48.9(3) C(2)-C()-C(0)-C(9) 78.7(2) C(2)-C()-C(7)-O() -62.3(3) C(2)-C()-C(7)-C(6) -78.7(2) C(2)-C()-C(7)-C(8) 57.2(3) C(2)-C(3)-C(4)-C(5) 59.5(3) C(2)-C(3)-C(4)-C() -.0(3) C(3)-C(4)-C(5)-C(6) -77.(2) C(3)-C(4)-C(5)-C(0) -59.6(3) C(3)-C(4)-C(5)-C() 63.7(3) C(4)-C(5)-C(6)-C(7) 72.(2) C(4)-C(5)-C(0)-C() 53.8(3) C(4)-C(5)-C(0)-C(9) -74.5(2) C(5)-C(6)-C(7)-C(8) -57.5(3) C(6)-C(5)-C(0)-C() 73.3(2) C(6)-C(5)-C(0)-C(9) -55.0(3) C(6)-C(7)-C(8)-C(9) 56.2(3) C(6)-C(7)-C(8)-C() -75.2(2) C(7)-C(8)-C(9)-C(0) -53.8(3) C(7)-C(8)-C(9)-C() 72.6(3) C(7)-C(8)-C(9)-C() -69.4(2) C(8)-C(9)-C(0)-C() -73.(2) C(8)-C(9)-C(0)-C(5) 54.8(3) C(8)-C(9)-C()-C(6) 73.66(9) C(9)-C()-C(6)-C(7) -6.5(3) C(9)-C()-C(6)-C() 6.4(3) C(0)-C()-C(2)-C(3) 46.5(3) C(0)-C()-C(7)-O() 6.4(2) C(0)-C()-C(7)-C(6) -55.(3) C(0)-C()-C(7)-C(8) -79.2(2) C(0)-C(5)-C(6)-C(7) 55.0(3) C(0)-C(9)-C()-C(6) 56.9(3) 59
60 C()-C(4)-C(5)-C(6) 3.4(4) C()-C(4)-C(5)-C(0) 0.9(3) C()-C(4)-C(5)-C() -5.8(3) C()-C(5)-C(6)-C(7) -70.8(3) C()-C(5)-C(0)-C() -64.0(3) C()-C(5)-C(0)-C(9) 67.7(3) C()-C(8)-C(9)-C(0) 79.9(2) C()-C(8)-C(9)-C() -53.7(3) C()-C(8)-C(9)-C() 64.3(3) C()-C(9)-C(0)-C() 62.4(3) C()-C(9)-C(0)-C(5) -69.8(3) C()-C(9)-C()-C(6) -66.2(3) C()-C(9)-C(0)-C() -56.5(3) C()-C(9)-C(0)-C(5) 7.3(2) C()-C(6)-C(7)-O() -57.2(3) C()-C(6)-C(7)-C() 58.6(3) C()-C(6)-C(7)-C(8) -78.0(2) C()-C(6)-C()-C(20) 79.5(3) C(6)-C(7)-C(8)-C(9) -2.5(4) C(7)-C()-C(2)-C(3) 68.6(2) C(7)-C()-C(0)-C(5) -70.5(2) C(7)-C()-C(0)-C(9) 57.2(3) C(7)-C(6)-C()-C(20) -2.8(5) C(7)-C(8)-C(9)-C(20) -0.3(5) C(8)-C(9)-C(20)-O(2) -78.9(3) C(8)-C(9)-C(20)-C().9(4) C(9)-C(20)-C()-C(6) -0.3(4) C()-C(6)-C(7)-O() 4.9(3) C()-C(6)-C(7)-C() -9.3(3) C()-C(6)-C(7)-C(8) 4.(4) Symmetry transformations used to generate equivalent atoms: 60
61 Table 7. Hydrogen bonds for cu_dm635_0m [Å and ]. D-H...A d(d-h) d(h...a) d(d...a) <(DHA) O()-H()...O(2)# (3) 74.3 Symmetry transformations used to generate equivalent atoms: # -x+,y+/2,-z+ 6
Cycloaddition of Homochiral Dihydroimidazoles: A 1,3-Dipolar Cycloaddition Route to Optically Active Pyrrolo[1,2-a]imidazoles
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