Asymmetric Total Synthesis of Fawcettimine-Type Lycopodium Alkaloid, Lycopoclavamine-A.
Kaneko, Hiroki; Takahashi, Shunsuke; Kogure, Noriyuki; Kitajima, Mariko; Takayama, Hiromitsu; The Journal of organic chemistry 84 (2019) 5645–5654; doi:10.1021/acs.joc.9b00586

data_4034345
_publ_section_title
;
 Asymmetric Total Synthesis of Fawcettimine-Type Lycopodium Alkaloid,
 Lycopoclavamine-A.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5645
_journal_page_last               5654
_journal_paper_doi               10.1021/acs.joc.9b00586
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C23 H29 F3 N2 O9 S2'
_chemical_formula_sum            'C23 H29 F3 N2 O9 S2'
_chemical_formula_weight         598.61
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_formula_units_Z            3
_cell_length_a                   14.4545(4)
_cell_length_b                   14.4545(4)
_cell_length_c                   11.1066(4)
_cell_measurement_reflns_used    10931
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.03
_cell_measurement_theta_min      3.53
_cell_volume                     2009.64(11)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_av_unetI/netI     0.1228
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21805
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.120
_diffrn_reflns_theta_max         68.120
_diffrn_reflns_theta_min         3.531
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.480
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             936.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.96
_refine_diff_density_min         -0.47
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2381 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0194(18)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.369
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1971
_refine_ls_R_factor_gt           0.1076
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2280
_refine_ls_wR_factor_ref         0.3012
_reflns_number_gt                2150
_reflns_number_total             4820
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo9b00586_si_002.cif
_cod_data_source_block           181227kogure2
_cod_original_cell_volume        2009.64(10)
_cod_database_code               4034345