Total Synthesis of (+)-3-Demethoxyerythratidinone and (+)-Erysotramidine via the Oxidative Amidation of a Phenol.
Paladino, Marco; Zaifman, Joshua; Ciufolini, Marco A.; Organic letters 17 (2015) 3422–3425; doi:10.1021/acs.orglett.5b01423

data_1520707
_publ_section_title
;
 Total Synthesis of (+)-3-Demethoxyerythratidinone and (+)-Erysotramidine
 via the Oxidative Amidation of a Phenol.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3422
_journal_page_last               3425
_journal_paper_doi               10.1021/acs.orglett.5b01423
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C20 H23 N O8'
_chemical_formula_weight         405.39
_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                   8.7215(6)
_cell_length_b                   11.3257(8)
_cell_length_c                   19.2170(10)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    90.0(1)
_cell_measurement_theta_max      67.6
_cell_measurement_theta_min      4.53
_cell_volume                     1898.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(1)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17984
_diffrn_reflns_theta_full        67.82
_diffrn_reflns_theta_max         67.82
_diffrn_reflns_theta_min         4.53
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0269
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0377P)^2^+0.4031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0672
_refine_ls_wR_factor_ref         0.0680
_reflns_number_gt                3286
_reflns_number_total             3374
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol5b01423_si_002.cif
_cod_data_source_block           mc049
_cod_depositor_comments          'Adding full bibliography for 1520707.cif.'
_cod_original_sg_symbol_H-M      'P 212121'
_cod_database_code               1520707