Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy Inspired by Chemical Network Analysis.
Owens, Kyle R.; McCowen, Shelby V.; Blackford, Katherine A.; Ueno, Sohei; Hirooka, Yasuo; Weber, Manuel; Sarpong, Richmond; Journal of the American Chemical Society 141 (2019) 13713–13717; doi:10.1021/jacs.9b05815

data_4128838
_publ_section_title
;
 Total Synthesis of the Diterpenoid Alkaloid Arcutinidine Using a Strategy
 Inspired by Chemical Network Analysis.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13713
_journal_page_last               13717
_journal_paper_doi               10.1021/jacs.9b05815
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C28 H35 N O4'
_chemical_formula_weight         449.57
_chemical_name_common            KO001
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
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_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 94.110(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7300(9)
_cell_length_b                   8.7313(6)
_cell_length_c                   20.2583(14)
_cell_measurement_reflns_used    9343
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.54
_cell_volume                     2245.9(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    Mercury
_computing_publication_material  WinGX
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_computing_structure_solution    'SHELXT (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
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_diffrn_reflns_limit_l_min       -26
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        28.000
_diffrn_reflns_theta_max         28.354
_diffrn_reflns_theta_min         1.832
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       Block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
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_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0667P)^2^+1.2137P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
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_reflns_number_gt                4877
_reflns_number_total             5589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05815_si_001.cif
_cod_data_source_block           KO001
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4128838
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              80005
_shelx_hkl_checksum              73258