Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide, 16-Hydroxytriptolide, and Their Analogues.
Xu, Hongtao; Tang, Huanyu; Feng, Huijin; Li, Yuanchao; The Journal of organic chemistry 79 (2014) 10110–; doi:10.1021/jo501744j

data_4030102
_publ_section_title
;
 Divergent Total Synthesis of Triptolide, Triptonide, Tripdiolide,
 16-Hydroxytriptolide, and Their Analogues.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10110
_journal_paper_doi               10.1021/jo501744j
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C18 H20 O5'
_chemical_formula_weight         316.34
_space_group_IT_number           56
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.8158(8)
_cell_length_b                   8.4490(3)
_cell_length_c                   14.6172(6)
_cell_measurement_temperature    296(2)
_cell_volume                     3064.77(19)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13887
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.100
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1989
_reflns_number_total             2667
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501744j_si_003.cif
_cod_data_source_block           2013396_0ma
_cod_depositor_comments
'Adding full bibliography for 4030102--4030103.cif.'
_cod_original_sg_symbol_H-M      Pccn
_cod_database_code               4030102