New facile enantio- and diastereo-selective syntheses of (-)-triptonide and (-)-triptolide.
Zhang, Hongrui; Li, Haifeng; Xue, Jijun; Chen, Rui; Li, Ying; Tang, Yu; Li, Chunxin; Organic & biomolecular chemistry 12 (2014) 732–736; doi:10.1039/c3ob42183j

data_7153600
_publ_section_title
;
 New facile enantio- and diastereo-selective syntheses of (-)-triptonide
 and (-)-triptolide.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              732
_journal_page_last               736
_journal_paper_doi               10.1039/c3ob42183j
_journal_volume                  12
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H24 O4'
_chemical_formula_sum            'C18 H24 O4'
_chemical_formula_weight         304.37
_chemical_name_systematic
;
?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-03-20
_audit_creation_method
;
Olex2 1.2
(compiled Dec 5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.576(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9067(10)
_cell_length_b                   7.6918(4)
_cell_length_c                   13.0515(13)
_cell_measurement_reflns_used    1213
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0250
_cell_measurement_theta_min      3.7390
_cell_volume                     1662.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_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
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9104
_diffrn_measurement_details
;
1 omega -13.00 20.00 1.5000 20.9100
omega____ theta____ kappa____ phi______ frames
- -19.3700 -99.0000 -120.0000 22

2 omega -97.00 -71.50 1.5000 20.9100
omega____ theta____ kappa____ phi______ frames
- -19.3700 178.0000 120.0000 17

3 omega -53.00 40.00 1.5000 20.9100
omega____ theta____ kappa____ phi______ frames
- 22.6512 0.0000 -120.0000 62

4 omega -11.00 79.00 1.5000 20.9100
omega____ theta____ kappa____ phi______ frames
- 22.6512 -19.0000 120.0000 60
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0049399000
_diffrn_orient_matrix_UB_12      -0.0236867000
_diffrn_orient_matrix_UB_13      0.0534321000
_diffrn_orient_matrix_UB_21      0.0419945000
_diffrn_orient_matrix_UB_22      0.0170995000
_diffrn_orient_matrix_UB_23      0.0072595000
_diffrn_orient_matrix_UB_31      -0.0068787000
_diffrn_orient_matrix_UB_32      0.0874115000
_diffrn_orient_matrix_UB_33      0.0131101000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3430
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.0(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.4885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                2295
_reflns_number_total             2760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob42183j.txt
_cod_data_source_block           chenrui_0318
_cod_database_code               7153600
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
{H7A,H7B} of C7, H4 of C4, H3 of C3, H2 of C2, {H13A,H13B} of C13, {H12A,
H12B} of C12, H9 of C9, {H8A,H8B} of C8, {H17A,H17B} of C17, H15 of C15
At 1.5 times of:
{H11A,H11B,H11C} of C11, {H19A,H19B,H19C} of C19, {H18A,H18B,H18C} of C18
2.a Ternary CH refined with riding coordinates:
C9(H9), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;