Total Syntheses of (-)-Kopsifoline D and (-)-Deoxoapodine: Divergent Total Synthesis via Late-Stage Key Strategic Bond Formation.
Lee, Kiyoun; Boger, Dale L.; Journal of the American Chemical Society 136 (2014) 3312–; doi:10.1021/ja500548e

data_4120626
_publ_section_title
;
 Total Syntheses of (-)-Kopsifoline D and (-)-Deoxoapodine: Divergent
 Total Synthesis via Late-Stage Key Strategic Bond Formation.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3312
_journal_paper_doi               10.1021/ja500548e
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H0 N2 O4'
_chemical_formula_weight         332.22
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7075(3)
_cell_length_b                   12.7478(6)
_cell_length_c                   25.5515(11)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.51
_cell_measurement_theta_min      3.88
_cell_volume                     2510.53(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16514
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         70.547
_diffrn_reflns_theta_min         3.459
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.879
_exptl_crystal_description       rod
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   0.918
_exptl_transmission_factor_min   0.893
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 1653 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4364
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    0.896
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                4246
_reflns_number_total             4364
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja500548e_si_004.cif
_cod_data_source_block           boger05
_cod_database_code               4120626
_shelxl_version_number           2013-3
_shelx_res_checksum              10827
_shelx_hkl_checksum              65572