Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane.
Coffinier, Romain; Assal, Mourad El; Peixoto, Philippe A.; Bosset, Cyril; Miqueu, Karinne; Sotiropoulos, Jean-Marc; Pouységu, Laurent; Quideau, Stéphane; Organic letters 18 (2016) 1120–; doi:10.1021/acs.orglett.6b00224

data_1542714
_publ_section_title
;
 Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative
 Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel
 Salen-Type Chiral Iodane.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1120
_journal_paper_doi               10.1021/acs.orglett.6b00224
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C30 H44 O4'
_chemical_formula_weight         468.65
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0564(2)
_cell_length_b                   12.2225(4)
_cell_length_c                   28.0933(6)
_cell_measurement_reflns_used    13676
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.738
_cell_measurement_theta_min      3.146
_cell_volume                     2766.33(13)
_computing_cell_refinement       'CrystalClear suite 1.36'
_computing_data_collection       'CrystalClear suite 1.36'
_computing_data_reduction        'CrystalClear suite 1.36'
_computing_molecular_graphics    'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXD (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'AFC11 partial chi goniometer'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13676
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.738
_diffrn_reflns_theta_min         3.146
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1272 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.16(19)
_refine_ls_extinction_coef       0.0020(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0777
_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^)+(0.1444P)^2^+0.2793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.2717
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.812
_reflns_number_gt                4234
_reflns_number_total             4933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00224_si_002.cif
_cod_data_source_block           shelxd
_cod_database_code               1542714
_shelx_estimated_absorpt_t_min   0.895
_shelx_estimated_absorpt_t_max   0.895
_shelxl_version_number           2013-4
_shelx_res_checksum              12532
_shelx_hkl_checksum              93001