Acid-catalysed iterative generation of o-quinone methides for the synthesis of dioxabicyclo[3.3.1]nonanes: total synthesis of myristicyclins A–B
Gharpure, Santosh J.; Jegadeesan, S.; Vishwakarma, Dharmendra S.; Chemical Communications  (2021) –; doi:10.1039/D1CC06146A

data_7129304
_publ_section_title
;
 Acid-catalysed iterative generation of o-quinone methides for the
 synthesis of dioxabicyclo[3.3.1]nonanes: total synthesis of
 myristicyclins A--B
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06146A
_journal_year                    2021
_chemical_formula_moiety         'C32 H36 O6'
_chemical_formula_sum            'C32 H36 O6'
_chemical_formula_weight         516.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-24
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4688(7)
_cell_length_b                   8.0297(5)
_cell_length_c                   46.845(3)
_cell_measurement_reflns_used    1708
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.1530
_cell_measurement_theta_min      3.5460
_cell_volume                     5442.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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   -135.00 -11.00   1.00    8.00    -- -101.00  72.00-180.00  124
  2  \w   -122.00  -8.00   1.00    8.00    --  -32.00 -72.00 -36.00  114
  3  \w   -191.00 -29.00   1.00    8.00    -- -101.00   0.00-180.00  162
  4  \w   -135.00 -11.00   1.00    8.00    -- -101.00  72.00 -36.00  124
  5  \w   -122.00 -43.00   1.00    8.00    --  -32.00   0.00 -36.00   79
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1052559000
_diffrn_orient_matrix_UB_12      -0.0130139000
_diffrn_orient_matrix_UB_13      0.0044294000
_diffrn_orient_matrix_UB_21      0.0131952000
_diffrn_orient_matrix_UB_22      -0.0281626000
_diffrn_orient_matrix_UB_23      -0.0322812000
_diffrn_orient_matrix_UB_31      0.0092513000
_diffrn_orient_matrix_UB_32      0.1892680000
_diffrn_orient_matrix_UB_33      -0.0045095000
_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  0.1785
_diffrn_reflns_av_unetI/netI     0.1429
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            19311
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        64.998
_diffrn_reflns_theta_max         64.998
_diffrn_reflns_theta_min         3.591
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       plate
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.0917
_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^)+(0.1484P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2347
_refine_ls_wR_factor_ref         0.3225
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2095
_reflns_number_total             4618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06146a2.cif
_cod_data_source_block           sjg-jsm-06-69-c_cu
_cod_original_cell_volume        5442.4(6)
_cod_database_code               7129304
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.874
_reflns_odcompleteness_completeness 98.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.57
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C18(H18A,H18B), C5(H5A,H5B), C8(H8A,H8B), C7(H7A,H7B), C26(H26A,
 H26B), C6(H6A,H6B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C13(H13), C22(H22), C23(H23), C32(H32), C31(H31), C28(H28),
 C30(H30), C29(H29)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_shelx_res_checksum              37678
_shelx_hkl_checksum              85623
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 16.999
_oxdiff_exptl_absorpt_empirical_full_min 0.412