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_7124940
_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_absolute_configuration syn
_chemical_formula_moiety         'C29 H28 N2 O'
_chemical_formula_sum            'C29 H28 N2 O'
_chemical_formula_weight         420.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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                 91.597(14)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.118(7)
_cell_length_b                   16.336(13)
_cell_length_c                   8.515(6)
_cell_measurement_reflns_used    617
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      5.20
_cell_volume                     1128.8(15)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b6'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b6 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b6'
_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    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11833
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.181
_diffrn_reflns_theta_min         5.197
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             448.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details
;
 No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   1.1(8)
_refine_ls_extinction_coef       0.0059(12)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0751P)^2^+0.7263P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1777
_reflns_Friedel_coverage         0.581
_reflns_Friedel_fraction_full    0.628
_reflns_Friedel_fraction_max     0.624
_reflns_number_gt                2564
_reflns_number_total             3369
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6cc05747k2.cif
_cod_data_source_block           5
_cod_database_code               7124940
_shelx_res_checksum              12469