Asymmetric Synthesis of Neolignans (-)-epi-Conocarpan and (+)-Conocarpan via Rh(II)-Catalyzed C-H Insertion Process and Revision of the Absolute Configuration of (-)-epi-Conocarpan
Yoshihiro Natori; Hideyuki Tsutsui; Naoki Sato; Seiichi Nakamura; Hisanori Nambu; Motoo Shiro; Shunichi Hashimoto; Journal of Organic Chemistry 74 (2009) 4418–4421; doi:10.1021/jo900502d

data_4024570
_publ_section_title
;
Asymmetric Synthesis of Neolignans (-)-epi-Conocarpan and (+)-Conocarpan
via Rh(II)-Catalyzed C-H Insertion Process and Revision of the Absolute
Configuration of (-)-epi-Conocarpan
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4418
_journal_page_last               4421
_journal_paper_doi               10.1021/jo900502d
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H26 N4 O3 '
_chemical_formula_sum            'C19 H26 N4 O3'
_chemical_formula_weight         358.44
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             2007-02-05
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.9192(10)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.8315(2)
_cell_length_b                   7.99869(14)
_cell_length_c                   11.1291(2)
_cell_measurement_reflns_used    9338
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      6.4
_cell_volume                     943.41(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (R/MSC, Rigaku, 2005)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (R/MSC, Rigaku, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10872
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.912
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     239
_refine_ls_number_reflns         1857
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.3071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                1781
_reflns_number_total             1857
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo900502d_si_003.cif
_cod_data_source_block           '_RGK1419'
_cod_original_formula_sum        'C19 H26 N4 O3 '
_cod_database_code               4024570