Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization.
Bellavance, Gabriel; Barriault, Louis; The Journal of organic chemistry 83 (2018) 7215–7230; doi:10.1021/acs.joc.8b00426

data_4035435
_publ_section_title
;
 Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via
 Gold(I)-Catalyzed Carbocyclization.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7215
_journal_page_last               7230
_journal_paper_doi               10.1021/acs.joc.8b00426
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C24 H36 O3 Si'
_chemical_formula_weight         400.62
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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_method           SHELXL-97
_cell_angle_alpha                73.285(3)
_cell_angle_beta                 85.172(3)
_cell_angle_gamma                89.787(3)
_cell_formula_units_Z            4
_cell_length_a                   10.5850(5)
_cell_length_b                   15.1637(7)
_cell_length_c                   15.7734(7)
_cell_measurement_reflns_used    2323
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.06
_cell_measurement_theta_min      2.71
_cell_volume                     2415.6(2)
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_collection       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0846
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21368
_diffrn_reflns_theta_full        22.72
_diffrn_reflns_theta_max         22.72
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         6492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0742
_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^)+(0.0760P)^2^+1.5949P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1603
_refine_ls_wR_factor_ref         0.1833
_reflns_number_gt                4332
_reflns_number_total             6492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00426_si_003.cif
_cod_data_source_block           lb083_5
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H72 O6 Si2'
_cod_original_formula_weight         801.24
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2415.62(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4035435