Enantioselective Formal Synthesis of (+)-Dihydrocorynantheine and (-)-Dihydrocorynantheol
Mercedes Amat; Arantxa Gómez-Esqué; Carmen Escolano; María M. M. Santos; Elies Molins; Joan Bosch; Journal of Organic Chemistry 74 (2009) 1205–1211; doi:10.1021/jo802387c

data_4024312
_publ_section_title
;
Enantioselective Formal Synthesis of (+)-Dihydrocorynantheine and
(-)-Dihydrocorynantheol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1205
_journal_page_last               1211
_journal_paper_doi               10.1021/jo802387c
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H28 N2 O3'
_chemical_formula_sum            'C21 H28 N2 O3'
_chemical_formula_weight         356.45
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-10-22T19:36:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                63.9020(10)
_cell_angle_beta                 77.89(2)
_cell_angle_gamma                67.88(4)
_cell_formula_units_Z            2
_cell_length_a                   8.351(4)
_cell_length_b                   10.977(2)
_cell_length_c                   12.4447(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.1
_cell_measurement_theta_min      9.6
_cell_measurement_wavelength     0.71073
_cell_volume                     947.7(6)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_orient_matrix_type
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.049721
_diffrn_orient_matrix_UB_12      -0.101762
_diffrn_orient_matrix_UB_13      0.008046
_diffrn_orient_matrix_UB_21      0.005309
_diffrn_orient_matrix_UB_22      0.033594
_diffrn_orient_matrix_UB_23      -0.089127
_diffrn_orient_matrix_UB_31      0.119389
_diffrn_orient_matrix_UB_32      0.003255
_diffrn_orient_matrix_UB_33      -0.004548
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3314
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.82
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.9402
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         3316
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0579P)^2^+0.1921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                3015
_reflns_number_total             3314
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802387c_si_003.cif
_cod_data_source_block           jb58t
_cod_database_code               4024312