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_7124943
_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 ad
_chemical_formula_moiety         'C29 H31 N3 O S'
_chemical_formula_sum            'C29 H31 N3 O S'
_chemical_formula_weight         469.64
_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             2015-09-20
_audit_creation_method           'by CrystalStructure 4.1'
_audit_update_record
;
2016-06-17 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.657(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   13.438(3)
_cell_length_b                   14.165(2)
_cell_length_c                   13.5796(19)
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    125
_cell_measurement_theta_max      74.60
_cell_measurement_theta_min      24.20
_cell_volume                     2579.6(8)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1235
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28126
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.342
_diffrn_reflns_theta_min         4.488
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.45
_refine_ls_abs_structure_details
;
 Flack x determined using 3168 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     627
_refine_ls_number_reflns         8712
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.2584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1522
_reflns_number_gt                8450
_reflns_number_total             8712
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c6cc05747k2.cif
_cod_data_source_block           15
_cod_database_code               7124943
_shelx_res_checksum              6766