An expedient approach to the total synthesis of (+)-5-epi-eudesm-4(15)-ene-1beta,6beta-diol
Gowrisankar Parthasarathy; Celine Besnard; E. Peter Kundig; Chem.Commun. 48 (2012) 11241–; doi:10.1039/c2cc36260k

data_7108575
_publ_section_title
;
 An expedient approach to the total synthesis of
 (+)-5-epi-eudesm-4(15)-ene-1beta,6beta-diol
;
_journal_name_full               Chem.Commun.
_journal_page_first              11241
_journal_paper_doi               10.1039/c2cc36260k
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C22 H32 O4'
_chemical_formula_sum            'C22 H32 O4'
_chemical_formula_weight         360.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-06-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled May 9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                111.977(4)
_cell_angle_beta                 93.290(3)
_cell_angle_gamma                95.850(3)
_cell_formula_units_Z            4
_cell_length_a                   10.9928(4)
_cell_length_b                   12.8258(5)
_cell_length_c                   15.6915(6)
_cell_measurement_reflns_used    12956
_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      73.2389
_cell_measurement_theta_min      3.0508
_cell_volume                     2029.95(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      180.00(14)
_diffrn_detector_area_resol_mean 10.4679
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
1 omega -70.00 37.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -37.6865 57.0000 60.0000 107

2 omega -116.00 -7.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -37.6865 -38.0000 -90.0000 109

3 omega -34.00 37.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -37.6865 38.0000 -30.0000 71

4 omega -49.00 41.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -37.6865 38.0000 -150.0000 90

5 omega -36.00 -7.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -37.6865 -57.0000 60.0000 29

6 omega -115.00 -44.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- -37.6865 -57.0000 60.0000 71

7 omega 17.00 43.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 37.6865 38.0000 -60.0000 26

8 omega 59.00 127.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 37.6865 178.0000 -150.0000 68

9 omega 3.00 79.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 37.6865 -99.0000 -90.0000 76

10 omega 92.00 117.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 37.6865 38.0000 -60.0000 25

11 omega 2.00 75.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 37.6865 77.0000 120.0000 73

12 omega 5.00 31.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 44.0000 88.0000 -46.0000 26

13 omega 9.00 35.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 48.0000 86.0000 153.0000 26

14 omega 10.00 35.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 48.0000 84.0000 10.0000 25

15 omega 9.00 34.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 48.0000 86.0000 -116.0000 25

16 omega 20.00 46.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 52.0000 79.0000 -114.0000 26

17 omega 19.00 45.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 56.0000 82.0000 27.0000 26

18 omega 19.00 44.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 56.0000 82.0000 61.0000 25

19 omega 33.00 108.00 1.0000 1.5000
omega____ theta____ kappa____ phi______ frames
- 68.0000 75.0000 165.0000 75

20 omega -59.00 -33.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 30.0000 26

21 omega -68.00 -32.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 -60.0000 36

22 omega -59.00 -33.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 132.0000 26

23 omega -57.00 -32.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 0.0000 25

24 omega -57.00 -32.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 -30.0000 25

25 omega -57.00 -32.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 -163.0000 25

26 omega -59.00 -34.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -75.0000 166.0000 25

27 omega -59.00 -33.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 60.0000 26

28 omega -61.00 -33.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 -120.0000 28

29 omega -59.00 -33.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -76.0000 85.0000 26

30 omega -58.00 -32.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- -68.5000 -77.0000 -90.0000 26

31 omega 79.00 134.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 61.0000 0.0000 55

32 omega 25.00 104.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 -94.0000 -60.0000 79

33 omega 74.00 144.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -150.0000 70

34 omega 74.00 145.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -90.0000 71

35 omega 36.00 89.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 -45.0000 -60.0000 53

36 omega 77.00 103.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 61.0000 30.0000 26

37 omega 24.00 104.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 -94.0000 -150.0000 80

38 omega 27.00 92.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 -94.0000 90.0000 65

39 omega 28.00 116.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 -111.0000 -180.0000 88

40 omega 75.00 142.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 60.0000 67

41 omega 74.00 138.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 120.0000 64

42 omega 74.00 177.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -180.0000 103

43 omega 74.00 167.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 90.0000 93

44 omega 111.00 177.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 30.0000 66

45 omega 78.00 103.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 61.0000 -30.0000 25

46 omega 81.00 107.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 61.0000 -90.0000 26

47 omega 60.00 109.00 1.0000 3.0000
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- 109.7499 -111.0000 60.0000 49

48 omega 75.00 101.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 30.0000 26

49 omega 74.00 178.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 0.0000 104

50 omega 78.00 105.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 61.0000 60.0000 27

51 omega 125.00 151.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -30.0000 26

52 omega 75.00 107.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -30.0000 32

53 omega 113.00 177.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -120.0000 64

54 omega 74.00 99.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -120.0000 25

55 omega 74.00 149.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
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56 omega 74.00 153.00 1.0000 3.0000
omega____ theta____ kappa____ phi______ frames
- 109.7499 77.0000 -60.0000 79
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1348305000
_diffrn_orient_matrix_UB_12      0.0482615000
_diffrn_orient_matrix_UB_13      0.0020794000
_diffrn_orient_matrix_UB_21      -0.0428755000
_diffrn_orient_matrix_UB_22      0.0801333000
_diffrn_orient_matrix_UB_23      -0.0447755000
_diffrn_orient_matrix_UB_31      -0.0066162000
_diffrn_orient_matrix_UB_32      0.0912697000
_diffrn_orient_matrix_UB_33      0.0965462000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30600
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         73.40
_diffrn_reflns_theta_min         3.05
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         8032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.4927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                6559
_reflns_number_total             8032
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36260k.txt
_cod_data_source_block           pgs_03_32
_cod_original_cell_volume        2029.94(13)
_cod_database_code               7108575
_chemical_oxdiff_formula         'C21 O3'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97