First total synthesis of asperilactone B. Revision of absolute stereochemistry of asperilactones B and C.
Djokić, Sanja; Benedeković, Goran; Kesić, Jelena; Rodić, Marko V; Popsavin, Mirjana; Popsavin, Velimir; Francuz, Jovana; Organic & biomolecular chemistry 22 (2024) 4864–4867; doi:10.1039/d4ob00583j

data_7159946
_publ_section_title
;
 First total synthesis of asperilactone B. Revision of absolute
 stereochemistry of asperilactones B and C.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4864
_journal_page_last               4867
_journal_paper_doi               10.1039/d4ob00583j
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_enantioexcess_bulk     1
_chemical_enantioexcess_bulk_technique OA
_chemical_formula_moiety         'C8 H12 O5'
_chemical_formula_sum            'C8 H12 O5'
_chemical_formula_weight         188.18
_chemical_melting_point          401
_chemical_name_common
' 3,6-Anhydro-2,8-dideoxy-L-glycero-D-ido-octono-1,4-lactone '
_chemical_name_systematic
' 3,6-Anhydro-2,8-dideoxy-L-glycero-D-ido-octono-1,4-lactone '
_chemical_optical_rotation       '[\a]^25^~D~ = +38.4 (c = 0.5, Me~2~CO)'
_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     dual
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-02-19 deposited with the CCDC.	2024-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.37102(6)
_cell_length_b                   12.47818(12)
_cell_length_c                   26.7627(3)
_cell_measurement_reflns_used    10051
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      71.8730
_cell_measurement_theta_min      3.2620
_cell_volume                     1793.65(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      1.00  74.00   1.00   10.00    --   36.28 -99.00 -90.00   73
  2  \w    -18.00  63.00   1.00   10.00    --   36.28 -77.00-150.00   81
  3  \w      1.00  74.00   1.00   10.00    --   36.28 -99.00  30.00   73
  4  \w    -18.00  63.00   1.00   10.00    --   36.28 -77.00 120.00   81
  5  \w     56.00 109.00   1.00   10.00    --   36.28-178.00   0.00   53
  6  \w     39.00 106.00   1.00   40.00    --  108.00 -94.00 -60.00   67
  7  \w    101.00 176.00   1.00   40.00    --  108.00  77.00-150.00   75
  8  \w     39.00 106.00   1.00   40.00    --  108.00 -94.00  90.00   67
  9  \w     41.00 126.00   1.00   40.00    --  108.00 -61.00-150.00   85
 10  \w     40.00 125.00   1.00   40.00    --  108.00 -45.00 -60.00   85
 11  \w     39.00 106.00   1.00   40.00    --  108.00 -94.00 150.00   67
 12  \w     41.00 126.00   1.00   40.00    --  108.00 -61.00 120.00   85
 13  \w     70.00 178.00   1.00   40.00    --  108.00  15.00 -30.00  108
 14  \w     20.00 104.00   1.00   10.00    --   36.28  57.00 -90.00   84
 15  \w     20.00 104.00   1.00   10.00    --   36.28  57.00   0.00   84
 16  \w     20.00 104.00   1.00   10.00    --   36.28  57.00-180.00   84
 17  \w     20.00 104.00   1.00   10.00    --   36.28  57.00  60.00   84
 18  \w     85.00 175.00   1.00   40.00    --  108.00  71.00-129.00   90
 19  \w     91.00 176.00   1.00   40.00    --  108.00  45.00   0.00   85
 20  \w     70.00 178.00   1.00   40.00    --  108.00  15.00-180.00  108
 21  \w     91.00 176.00   1.00   40.00    --  108.00  45.00  90.00   85
 22  \w     70.00 178.00   1.00   40.00    --  108.00  15.00  90.00  108
 23  \w     39.00 106.00   1.00   40.00    --  108.00 -94.00   0.00   67
 24  \w     87.00 178.00   1.00   40.00    --  108.00  30.00-150.00   91
 25  \w     91.00 176.00   1.00   40.00    --  108.00  45.00 -90.00   85
 26  \w     17.00 106.00   1.00   10.00    --   36.28  37.00 150.00   89
 27  \w     20.00 104.00   1.00   10.00    --   36.28  57.00 -30.00   84
 28  \w    -31.00  53.00   1.00   10.00    --   36.28 -57.00 -60.00   84
 29  \w    -33.00  55.00   1.00   10.00    --   36.28 -37.00   0.00   88
 30  \w     90.00 155.00   1.00   40.00    --  108.00  61.00 -30.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S (Oxford Diffraction)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2268075000
_diffrn_orient_matrix_UB_12      -0.0518766000
_diffrn_orient_matrix_UB_13      -0.0256577000
_diffrn_orient_matrix_UB_21      0.0557309000
_diffrn_orient_matrix_UB_22      -0.1064572000
_diffrn_orient_matrix_UB_23      0.0269296000
_diffrn_orient_matrix_UB_31      -0.1665101000
_diffrn_orient_matrix_UB_32      0.0350280000
_diffrn_orient_matrix_UB_33      0.0439097000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19203
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.303
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.622
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.087
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
; 
 Flack x determined using 1195 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0332P)^2^+0.3008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3032
_reflns_number_total             3176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00583j3.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 7159944--7159948.cif.'
_cod_database_code               7159946
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              62529