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_4120624
_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_formula_sum            'C28 H30 N2 O3'
_chemical_formula_weight         442.54
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 100.631(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.306(5)
_cell_length_b                   6.569(4)
_cell_length_c                   21.010(11)
_cell_measurement_reflns_used    1736
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.50
_cell_volume                     1126.7(11)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       '\f and \w 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  0.0798
_diffrn_reflns_av_sigmaI/netI    0.1074
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10697
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9907
_exptl_absorpt_correction_type   'not measured'
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallalepiped
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       0.045(6)
_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   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.378
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1800
_reflns_number_gt                2112
_reflns_number_total             3969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja500548e_si_002.cif
_cod_data_source_block           klab_0m
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1126.6(11)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4120624