Asymmetric total synthesis of penicilfuranone A through an NHC-catalyzed umpolung strategy
Ding, Yiming; Long, Xianwen; Zhang, Jingwei; Qu, Chunlei; Wang, Peng; Yang, Xiaodong; Puno, Pema-Tenzin; Deng, Jun; Chemical Science 16 (2025) 8302–8308; doi:10.1039/D5SC01508A

data_1574365
_publ_section_title
;
 Asymmetric total synthesis of penicilfuranone A through an NHC-catalyzed
 umpolung strategy
;
_journal_issue                   19
_journal_name_full               'Chemical Science'
_journal_page_first              8302
_journal_page_last               8308
_journal_paper_doi               10.1039/D5SC01508A
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C21 H24 O6'
_chemical_formula_sum            'C21 H24 O6'
_chemical_formula_weight         372.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-03-24
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-04-02 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.262(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9343(2)
_cell_length_b                   19.9249(5)
_cell_length_c                   11.1682(4)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    104(7)
_cell_measurement_theta_max      35.4470
_cell_measurement_theta_min      2.7650
_cell_volume                     1908.57(10)
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      104(7)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.852
_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    -45.00   7.00   0.50    0.15    --   10.00 -55.00 109.78  104
  2  \w    -45.00   7.00   0.50    0.15    --   10.00 -53.00  26.65  104
  3  \w    -48.00 -23.00   0.50    0.15    --   10.00 -38.00-157.75   50
  4  \w     -8.00  48.00   0.50    0.15    --  -10.00  44.00-160.85  112
  5  \w    -49.00 -20.00   0.50    0.15    --  -10.00 130.00-140.81   58
  6  \w    -54.00 -25.00   0.50    0.15    --  -10.00 137.00  41.68   58
  7  \w     -2.00  28.00   0.50    0.15    --   -0.18  72.00 127.67   60
  8  \w      9.00  35.00   0.50    0.15    --   -0.18-123.00 165.50   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0811668000
_diffrn_orient_matrix_UB_12      0.0022385000
_diffrn_orient_matrix_UB_13      -0.0297296000
_diffrn_orient_matrix_UB_21      0.0043687000
_diffrn_orient_matrix_UB_22      0.0354938000
_diffrn_orient_matrix_UB_23      0.0047501000
_diffrn_orient_matrix_UB_31      0.0152987000
_diffrn_orient_matrix_UB_32      0.0017490000
_diffrn_orient_matrix_UB_33      -0.0588859000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.904
_diffrn_reflns_theta_min         2.585
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         7654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1602
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5534
_reflns_number_total             7654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01508a2.cif
_cod_data_source_block           37-mr-20250323a_auto
_cod_depositor_comments
'Adding full bibliography for 1574363--1574365.cif.'
_cod_database_code               1574365
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C009(H009), C00F(H00F)
1.b Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00B)
1.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00K(H00K), C00N(H00N)
1.d Idealised Me refined as rotating group:
 C00M(H00C,H00D,H00E), C00O(H00I,H00J,H00L), C00P(H00M,H00O,H00P), C00Q(H00Q,
 H00R,H00S), C00R(H00T,H00U,H00V)
1.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              51151
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.368
_oxdiff_exptl_absorpt_empirical_full_min 0.575