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_4120225
_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 rmad
_chemical_formula_sum            'C29 H35 Br N2 O3'
_chemical_formula_weight         539.50
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3410(6)
_cell_length_b                   15.7811(13)
_cell_length_c                   22.181(2)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.92
_cell_volume                     2569.6(4)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  '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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            48335
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  0.8537
_exptl_absorpt_correction_T_min  0.5269
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0463P)^2^+0.4756P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                4772
_reflns_number_total             5875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja405548b_si_001.cif
_cod_data_source_block           wood25
_cod_original_cell_volume        2569.7(4)
_cod_database_code               4120225