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_7159948
_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          397
_chemical_name_common
' 3,6-Anhydro-2,8-dideoxy-D-glycero-L-gluco-octono-1,4-lactone '
_chemical_name_systematic
' 3,6-Anhydro-2,8-dideoxy-D-glycero-L-gluco-octono-1,4-lactone '
_chemical_optical_rotation       '[\a]^25^~D~ = +29.0 (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   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_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            4
_cell_length_a                   5.48541(5)
_cell_length_b                   10.62294(8)
_cell_length_c                   15.21442(14)
_cell_measurement_reflns_used    10930
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      71.8490
_cell_measurement_theta_min      2.8840
_cell_volume                     886.562(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'ShelXle (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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 (Oxford Diffraction)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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      7.00 108.00   1.00    3.00    --   36.41  19.00 120.00  101
  2  \w     22.00  90.00   1.00    3.00    --   36.41-125.00-150.00   68
  3  \w     20.00 104.00   1.00    3.00    --   36.41  57.00 120.00   84
  4  \w     22.00  90.00   1.00    3.00    --   36.41-125.00   0.00   68
  5  \w     39.00 106.00   1.00   12.00    --  108.00 -94.00-180.00   67
  6  \w    104.00 178.00   1.00   12.00    --  108.00 111.00 -90.00   74
  7  \w    101.00 176.00   1.00   12.00    --  108.00  77.00-120.00   75
  8  \w     41.00 126.00   1.00   12.00    --  108.00 -61.00-120.00   85
  9  \w     91.00 176.00   1.00   12.00    --  108.00  45.00  60.00   85
 10  \w     39.00 106.00   1.00   12.00    --  108.00 -94.00  60.00   67
 11  \w     39.00 106.00   1.00   12.00    --  108.00 -94.00 -90.00   67
 12  \w     39.00 106.00   1.00   12.00    --  108.00 -94.00  30.00   67
 13  \w     90.00 175.00   1.00   12.00    --  108.00  61.00-150.00   85
 14  \w     20.00 104.00   1.00    3.00    --   36.41  57.00-150.00   84
 15  \w    -31.00  53.00   1.00    3.00    --   36.41 -57.00  60.00   84
 16  \w     15.00 103.00   1.00    3.00    --   36.41  67.00 -86.00   88
 17  \w     20.00 104.00   1.00    3.00    --   36.41  57.00   0.00   84
 18  \w     91.00 176.00   1.00   12.00    --  108.00  45.00  30.00   85
 19  \w     90.00 175.00   1.00   12.00    --  108.00  61.00 -60.00   85
 20  \w     87.00 178.00   1.00   12.00    --  108.00  30.00 150.00   91
 21  \w     91.00 176.00   1.00   12.00    --  108.00  45.00-180.00   85
 22  \w     87.00 178.00   1.00   12.00    --  108.00  30.00   0.00   91
 23  \w     87.00 178.00   1.00   12.00    --  108.00  30.00 -90.00   91
 24  \w    101.00 176.00   1.00   12.00    --  108.00  77.00   0.00   75
 25  \w     91.00 176.00   1.00   12.00    --  108.00  52.00  95.00   85
 26  \w    -31.00  53.00   1.00    3.00    --   36.41 -57.00-180.00   84
 27  \w    -33.00  56.00   1.00    3.00    --   36.41 -37.00 120.00   89
 28  \w    -31.00  53.00   1.00    3.00    --   36.41 -57.00 -30.00   84
 29  \w     20.00 104.00   1.00    3.00    --   36.41  57.00  60.00   84
 30  \w     90.00 175.00   1.00   12.00    --  108.00  61.00-180.00   85
 31  \w    104.00 178.00   1.00   12.00    --  108.00 111.00 -30.00   74
 32  \w     90.00 175.00   1.00   12.00    --  108.00  61.00 150.00   85
 33  \w     91.00 176.00   1.00   12.00    --  108.00  45.00   0.00   85
 34  \w     87.00 178.00   1.00   12.00    --  108.00  30.00 -60.00   91
 35  \w     91.00 176.00   1.00   12.00    --  108.00  45.00 120.00   85
 36  \w     91.00 176.00   1.00   12.00    --  108.00  45.00  90.00   85
 37  \w     91.00 176.00   1.00   12.00    --  108.00  45.00-150.00   85
 38  \w     20.00  71.00   1.00    3.00    --   36.41  57.00 150.00   51
 39  \w      1.00  75.00   1.00    3.00    --   36.41 -99.00 -60.00   74
;
_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      -0.1882033000
_diffrn_orient_matrix_UB_12      -0.0612880000
_diffrn_orient_matrix_UB_13      0.0617780000
_diffrn_orient_matrix_UB_21      -0.0985167000
_diffrn_orient_matrix_UB_22      0.1312231000
_diffrn_orient_matrix_UB_23      0.0244482000
_diffrn_orient_matrix_UB_31      -0.1836494000
_diffrn_orient_matrix_UB_32      -0.0075443000
_diffrn_orient_matrix_UB_33      -0.0764263000
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13317
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.945
_diffrn_reflns_theta_min         5.078
_diffrn_source
'fine-focus sealed X-ray tube (Oxford Diffraction)'
_diffrn_source_type
'Enhance (Cu) X-ray Source (Oxford Diffraction)'
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.555
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.41.109a (Rigaku Oxford Diffraction, 2021) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       0.058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0523P)^2^+0.1071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0872
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1716
_reflns_number_total             1726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00583j3.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 7159944--7159948.cif.'
_cod_original_cell_volume        886.561(13)
_cod_database_code               7159948
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.521
_shelx_estimated_absorpt_t_max   0.847
_shelx_res_checksum              99269