An Enantioselective Total Synthesis and Stereochemical Revision of (+)-Citrinadin B
Ke Kong; John A. Enquist; Monica E. McCallum; Genessa M. Smith; Takanori Matsumaru; Elnaz Menhaji-Klotz; John L. Wood; Journal of the American Chemical Society 135 (2013) 10890–10893; doi:10.1021/ja405548b

data_4120226
_publ_section_title
;
 An Enantioselective Total Synthesis and Stereochemical Revision of
 (+)-Citrinadin B
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10890
_journal_page_last               10893
_journal_paper_doi               10.1021/ja405548b
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_sum            'C28 H32 N2 O3'
_chemical_formula_weight         444.56
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Bruker SHELXTL'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4679(3)
_cell_length_b                   13.9184(6)
_cell_length_c                   21.9214(9)
_cell_measurement_reflns_used    9395
_cell_measurement_temperature    100(2)
_cell_volume                     2278.54(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker-AXS Apex 2 CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0499
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            63534
_diffrn_reflns_theta_full        33.50
_diffrn_reflns_theta_max         33.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1997'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       cube
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0008(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         8839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0697P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                7199
_reflns_number_total             8839
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja405548b_si_002.cif
_cod_data_source_block           wood01_0m
_cod_database_code               4120226