Total synthesis of exigurin: the Ugi reaction in a hypothetical biosynthesis of natural products.
Hosokawa, Seijiro; Nakanishi, Keisuke; Udagawa, Yutaro; Maeda, Mitsutoshi; Sato, Seiya; Nakano, Keiji; Masuda, Toshiya; Ichikawa, Yoshiyasu; Organic & biomolecular chemistry 18 (2020) 687–693; doi:10.1039/c9ob02249j

data_7157293
_publ_section_title
;
 Total synthesis of exigurin: the Ugi reaction in a hypothetical
 biosynthesis of natural products.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              687
_journal_page_last               693
_journal_paper_doi               10.1039/c9ob02249j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C20 H26 O3 S'
_chemical_formula_sum            'C20 H26 O3 S'
_chemical_formula_weight         346.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-07-25 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.14999(13)
_cell_length_b                   12.6963(2)
_cell_length_c                   20.1516(4)
_cell_measurement_reflns_used    21350
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      3.48
_cell_volume                     1829.33(6)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_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  0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20894
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.178
_diffrn_reflns_theta_min         4.116
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.683
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744.00
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.52
_refine_ls_abs_structure_details
;
 Flack x determined using 1296 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.078(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0629P)^2^+0.6196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0967
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                3191
_reflns_number_total             3213
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c9ob02249j2.cif
_cod_data_source_block           20190724_B_cyclo2_nakanish
_cod_depositor_comments
'Adding full bibliography for 7157293--7157294.cif.'
_cod_database_code               7157293
_shelxl_version_number           2014/6
_shelx_res_checksum              17486