Total synthesis of (+/-)-stemonamide and (+/-)-isostemonamide using a radical cascade.
Taniguchi, Tsuyoshi; Tanabe, Genzo; Muraoka, Osamu; Ishibashi, Hiroyuki; Organic letters 10 (2008) 197–199; doi:10.1021/ol702563p

data_1504479
_publ_section_title
;
 Total synthesis of (+/-)-stemonamide and (+/-)-isostemonamide using a
 radical cascade.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              197
_journal_page_last               199
_journal_paper_doi               10.1021/ol702563p
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C24 H27 N O4 '
_chemical_formula_sum            'C24 H27 N O4'
_chemical_formula_weight         393.48
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.147(4)
_cell_length_b                   18.976(7)
_cell_length_c                   9.467(3)
_cell_measurement_temperature    123.0
_cell_volume                     2002.5(12)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8.0'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.180
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18331
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840.00
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.64
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2124 Friedel Pairs'
_refine_ls_abs_structure_Flack   5(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4562
_refine_ls_R_factor_gt           0.1711
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1697P)^2^+12.1361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.4527
_reflns_number_gt                2730
_reflns_number_total             4562
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol702563p-file003.cif
_cod_data_source_block           '_shelxl'
_cod_original_formula_sum        'C24 H27 N O4 '
_cod_database_code               1504479