Asymmetric Total Synthesis of Kopsiyunnanine K, a Monoterpenoid Indole Alkaloid with a Rearranged Skeleton.
Tokuda, Ryoko; Okamoto, Yoshiki; Koyama, Tetsuya; Kogure, Noriyuki; Kitajima, Mariko; Takayama, Hiromitsu; Organic letters 18 (2016) 3490–3493; doi:10.1021/acs.orglett.6b01704

data_1555635
_publ_section_title
;
 Asymmetric Total Synthesis of Kopsiyunnanine K, a Monoterpenoid Indole
 Alkaloid with a Rearranged Skeleton.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3490
_journal_page_last               3493
_journal_paper_doi               10.1021/acs.orglett.6b01704
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H26 N2 O2'
_chemical_formula_sum            'C20 H26 N2 O2'
_chemical_formula_weight         326.44
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.01057(16)
_cell_length_b                   10.9727(2)
_cell_length_c                   17.5326(4)
_cell_measurement_reflns_used    10344
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.14
_cell_measurement_theta_min      4.03
_cell_volume                     1733.45(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_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  0.0321
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18530
_diffrn_reflns_theta_full        68.14
_diffrn_reflns_theta_max         68.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_correction_T_min  0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.180
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1335 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0016(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.3857P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                2885
_reflns_number_total             3159
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol6b01704_si_002.cif
_cod_data_source_block           141216kogure1
_cod_database_code               1555635