Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids: Enantioselective Synthesis of (-)-Cermizine B, (+)-Serratezomine E, and (+)-Luciduline.
Pinto, Alexandre; Piccichè, Miriam; Griera, Rosa; Molins, Elies; Bosch, Joan; Amat, Mercedes; The Journal of organic chemistry 83 (2018) 8364–8375; doi:10.1021/acs.joc.8b00983

data_4035554
_publ_section_title
;
 Studies on the Synthesis of Phlegmarine-Type Lycopodium Alkaloids:
 Enantioselective Synthesis of (-)-Cermizine B, (+)-Serratezomine E, and
 (+)-Luciduline.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8364
_journal_page_last               8375
_journal_paper_doi               10.1021/acs.joc.8b00983
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2017-10-26T15:18:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 113.74(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.070(5)
_cell_length_b                   6.411(3)
_cell_length_c                   11.639(3)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.62
_cell_measurement_theta_min      7.46
_cell_measurement_wavelength     0.71073
_cell_volume                     1507.5(9)
_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, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled \w scans'
_diffrn_orient_matrix_type
'x-axis points to radiation source - matrix specified in reciprocal space'
_diffrn_orient_matrix_UB_11      0.047581
_diffrn_orient_matrix_UB_12      -0.04343
_diffrn_orient_matrix_UB_13      0.033307
_diffrn_orient_matrix_UB_21      -0.005317
_diffrn_orient_matrix_UB_22      -0.038806
_diffrn_orient_matrix_UB_23      -0.086724
_diffrn_orient_matrix_UB_31      0.012734
_diffrn_orient_matrix_UB_32      0.144653
_diffrn_orient_matrix_UB_33      -0.013506
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1532
_diffrn_reflns_point_group_measured_fraction_full 0.546
_diffrn_reflns_point_group_measured_fraction_max 0.546
_diffrn_reflns_theta_full        24.971
_diffrn_reflns_theta_max         24.971
_diffrn_reflns_theta_min         1.911
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.21
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1456
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0445
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.1022P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0
_reflns_Friedel_fraction_full    0
_reflns_Friedel_fraction_max     0
_reflns_number_gt                1104
_reflns_number_total             1456
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00983_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4035554