1,6-Hydroolefination and Cascade Cyclization of p-Quinone Methides with Styrenes: Total Synthesis of (±)-Isopaucifloral F.
Jadhav, Abhijeet S.; Pankhade, Yogesh A.; Hazra, Raju; Anand, Ramasamy Vijaya; The Journal of organic chemistry 83 (2018) 10107–10119; doi:10.1021/acs.joc.8b01401

data_4035128
_publ_section_title
;
 1,6-Hydroolefination and Cascade Cyclization of p-Quinone Methides with
 Styrenes: Total Synthesis of (+-)-Isopaucifloral F.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10107
_journal_page_last               10119
_journal_paper_doi               10.1021/acs.joc.8b01401
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C43 H42 O'
_chemical_formula_sum            'C43 H42 O'
_chemical_formula_weight         574.76
_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             2017-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3105(6)
_cell_length_b                   18.8797(8)
_cell_length_c                   24.8734(11)
_cell_measurement_reflns_used    7515
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7760
_cell_measurement_theta_min      3.0320
_cell_volume                     6720.2(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_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    -69.00 118.20   0.30   20.00    --   29.89  54.00   0.00  624
  2  \w     77.00 117.20   0.30   20.00    --   29.89  54.00-180.00  134
  3  \w    -68.00  30.10   0.30   20.00    --   29.89  54.00   0.00  327
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0009276000
_diffrn_orient_matrix_UB_12      0.0026761000
_diffrn_orient_matrix_UB_13      -0.0284483000
_diffrn_orient_matrix_UB_21      -0.0165647000
_diffrn_orient_matrix_UB_22      -0.0353199000
_diffrn_orient_matrix_UB_23      -0.0016842000
_diffrn_orient_matrix_UB_31      -0.0466970000
_diffrn_orient_matrix_UB_32      0.0125225000
_diffrn_orient_matrix_UB_33      0.0011457000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33410
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.709
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
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    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5903
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0608P)^2^+1.6963P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1299
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4709
_reflns_number_total             5903
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01401_si_002.cif
_cod_data_source_block           21a
_cod_database_code               4035128
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T),
 C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012)
2.d Idealised Me refined as rotating group:
 C013(H01A,H01B,H01C), C014(H01D,H01E,H01F), C015(H01G,H01H,H01I), C016(H01J,
 H01K,H01L), C017(H01M,H01N,H01O), C018(H01P,H01Q,H01R)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              89053
_shelx_hkl_checksum              34412
_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 1.703
_oxdiff_exptl_absorpt_empirical_full_min 0.705