Protecting-group-free total syntheses of (-)-integrifolin, (+)-8-<i>epi</i>-grosheimin and (+)-grosheimin.
Fernandes, Rodney A.; Gorve, Dnyaneshwar A.; Ramakrishna, Gujjula V.; Organic & biomolecular chemistry 23 (2025) 8059–8062; doi:10.1039/d5ob01078k

data_7160682
_publ_section_title
;
 Protecting-group-free total syntheses of (-)-integrifolin,
 (+)-8-<i>epi</i>-grosheimin and (+)-grosheimin.
;
_journal_issue                   35
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8059
_journal_page_last               8062
_journal_paper_doi               10.1039/d5ob01078k
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H22 O4'
_chemical_formula_sum            'C17 H22 O4'
_chemical_formula_weight         290.34
_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_date             2024-10-16
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2024-10-16 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9109(2)
_cell_length_b                   15.2939(7)
_cell_length_c                   17.2390(10)
_cell_measurement_reflns_used    1373
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      21.0840
_cell_measurement_theta_min      1.7740
_cell_volume                     1558.42(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -127.56  18.44   1.00    1.00    --  -22.85 -59.25  20.08  146
  2  \w   -127.56  18.44   1.00    1.00    --  -22.85 -59.25  71.08  146
  3  \f    -38.01 105.99   1.00    1.00  26.42 -22.85 -31.50    --   144
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0133031000
_diffrn_orient_matrix_UB_12      -0.0088197000
_diffrn_orient_matrix_UB_13      0.0401337000
_diffrn_orient_matrix_UB_21      -0.0092838000
_diffrn_orient_matrix_UB_22      -0.0454578000
_diffrn_orient_matrix_UB_23      -0.0075168000
_diffrn_orient_matrix_UB_31      0.1188970000
_diffrn_orient_matrix_UB_32      -0.0025395000
_diffrn_orient_matrix_UB_33      -0.0050904000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1679
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12043
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.780
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0678
_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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1791
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1807
_reflns_number_total             2738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01078k2.cif
_cod_data_source_block           raf_dg_bar_autored
_cod_depositor_comments          'Adding full bibliography for 7160682.cif.'
_cod_database_code               7160682
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 92.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.24
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C13(H13), C1(H1), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.d X=CH2 refined with riding coordinates:
 C5(H5A,H5B), C17(H17A,H17B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              44524
_olex2_submission_special_instructions 'No special instructions were received'