A Formal Synthesis of Ezetimibe via Cycloaddition/Rearrangement Cascade Reaction
Michał Michalak; Maciej Stodulski; Sebastian Stecko; Adam Mames; Irma Panfil; Magdalena Soluch; Bartłomiej Furman; Marek Chmielewski; Journal of Organic Chemistry 76 (2011) 6931–6936; doi:10.1021/jo2010846

data_4026521
_publ_section_title
;
 A Formal Synthesis of Ezetimibe via Cycloaddition/Rearrangement Cascade
 Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6931
_journal_page_last               6936
_journal_paper_doi               10.1021/jo2010846
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C27 H26 F N O4'
_chemical_formula_sum            'C27 H26 F N O4'
_chemical_formula_weight         447.49
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.439(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.995(4)
_cell_length_b                   5.7088(9)
_cell_length_c                   35.394(5)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.170
_cell_measurement_theta_min      2.4275
_cell_volume                     4339.9(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'WINGX, MERCURY, ORTEP'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Kappa ApexII Ultra CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            19846
_diffrn_reflns_theta_full        27.37
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_min         1.18
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  SADABS-2004/1 - Bruker Nonius area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       prosmatic
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     789
_refine_ls_number_reflns         9292
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0399
_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^)+(0.0337P)^2^+2.1741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                8300
_reflns_number_total             9292
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2010846_si_002.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        4340.0(12)
_cod_database_code               4026521