Total Synthesis of (-)-Oridonin: An Interrupted Nazarov Approach.
Kong, Lingran; Su, Fan; Yu, Hang; Jiang, Zhe; Lu, Yandong; Luo, Tuoping; Journal of the American Chemical Society 141 (2019) 20048–20052; doi:10.1021/jacs.9b12034

data_4133749
_publ_section_title
;
 Total Synthesis of (-)-Oridonin: An Interrupted Nazarov Approach.
;
_journal_issue                   51
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              20048
_journal_page_last               20052
_journal_paper_doi               10.1021/jacs.9b12034
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C27 H32 O3'
_chemical_formula_weight         404.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3651(2)
_cell_length_b                   18.5633(7)
_cell_length_c                   19.1960(8)
_cell_measurement_reflns_used    3291
_cell_measurement_temperature    179.99(17)
_cell_measurement_theta_max      23.3700
_cell_measurement_theta_min      2.1960
_cell_volume                     2268.15(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(17)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10273
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.194
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       rod-like
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1177 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0637P)^2^+0.7750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1571
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                3698
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b12034_si_004.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 4133749--4133753.cif.'
_cod_database_code               4133749
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              17612
_shelx_hkl_checksum              16948