Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction.
Wilkie, Ross P.; Neal, Andrew R.; Johnston, Craig A.; Voute, Nicholas; Lancefield, Christopher S.; Stell, Matthew D.; Medda, Federico; Makiyi, Edward F.; Turner, Emma M.; Stephen Ojo, O.; Slawin, Alexandra M. Z.; Lebl, Tomas; Mullen, Peter; Harrison, David J.; Ireland, Chris M.; Westwood, Nicholas J.; Chemical communications (Cambridge, England) 52 (2016) 10747–10750; doi:10.1039/c6cc05747k

data_7124941
_publ_section_title
;
 Total synthesis of dehaloperophoramidine using a highly
 diastereoselective Hosomi-Sakurai reaction.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10747
_journal_page_last               10750
_journal_paper_doi               10.1039/c6cc05747k
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C41 H38 N4 O2'
_chemical_formula_sum            'C41 H38 N4 O2'
_chemical_formula_weight         618.78
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-25
_audit_creation_method           'by CrystalStructure 4.2'
_audit_update_record
;
2016-05-04 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_formula_units_Z            9
_cell_length_a                   24.722(4)
_cell_length_b                   24.722(4)
_cell_length_c                   13.524(2)
_cell_measurement_reflns_used    8344
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.85
_cell_volume                     7158(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, ????)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.315
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14358
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         27.299
_diffrn_reflns_theta_min         2.854
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2952.00
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         1.37
_refine_diff_density_min         -0.65
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0946P)^2^+31.2290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2731
_reflns_number_total             3186
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6cc05747k2.cif
_cod_data_source_block           S16
_cod_original_cell_volume        7158.1(19)
_cod_original_sg_symbol_H-M      'R -3:H'
_cod_database_code               7124941
_shelx_res_checksum              48936