Total Synthesis of (±)-Cephanolides B and C via a Palladium-Catalyzed Cascade Cyclization and Late-Stage sp<sup>3</sup> C-H Bond Oxidation.
Xu, Lun; Wang, Chao; Gao, Ziwei; Zhao, Yu-Ming; Journal of the American Chemical Society 140 (2018) 5653–5658; doi:10.1021/jacs.8b03015

data_4132355
_publ_section_title
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 Total Synthesis of (+-)-Cephanolides B and C via a Palladium-Catalyzed
 Cascade Cyclization and Late-Stage sp<sup>3</sup> C-H Bond Oxidation.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5653
_journal_page_last               5658
_journal_paper_doi               10.1021/jacs.8b03015
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C19 H20 O4'
_chemical_formula_sum            'C19 H20 O4'
_chemical_formula_weight         312.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.2690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5021(3)
_cell_length_b                   7.11540(10)
_cell_length_c                   16.3667(3)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    273
_cell_measurement_theta_max      68.222
_cell_measurement_theta_min      3.370
_cell_volume                     1527.25(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20895
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.258
_diffrn_reflns_theta_min         3.370
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0850 before and 0.0399 after correction. The Ratio of minimum to maximum transmission is 0.7728. The \l/2 correction factor is Not present.'
_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    1.358
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0370
_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^)+(0.0571P)^2^+0.3558P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1042
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2618
_reflns_number_total             2776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b03015_si_006.cif
_cod_data_source_block           s
_cod_database_code               4132355
_shelx_shelxl_version_number     2014/7
_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:
 C007(H007), C009(H009), C00D(H00D), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B), C00I(H00C,H00E), C00J(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00F(H00F)
2.d Idealised Me refined as rotating group:
 C00K(H00I,H00J,H00K), C00M(H00M,H00N,H00O), C00N(H00P,H00Q,H00R)
;
_shelx_res_checksum              66881
_shelx_hkl_checksum              61781
_olex2_submission_special_instructions 'No special instructions were received'