Total Synthesis of Salimabromide: A Tetracyclic Polyketide from a Marine Myxobacterium.
Schmid, Matthias; Grossmann, Adriana S.; Wurst, Klaus; Magauer, Thomas; Journal of the American Chemical Society 140 (2018) 8444–8447; doi:10.1021/jacs.8b06228

data_4132770
_publ_section_title
;
 Total Synthesis of Salimabromide: A Tetracyclic Polyketide from a Marine
 Myxobacterium.
;
_journal_issue                   27
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8444
_journal_page_last               8447
_journal_paper_doi               10.1021/jacs.8b06228
_journal_volume                  140
_journal_year                    2018
_chemical_formula_sum            'C20 H22 O3'
_chemical_formula_weight         310.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.715(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.498(6)
_cell_length_b                   7.6508(18)
_cell_length_c                   15.583(4)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      24.0
_cell_measurement_theta_min      2.6
_cell_volume                     3278.1(13)
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL-XT-2014/4 (Bruker AXS, 2014)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 10.4
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26356
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        24.000
_diffrn_reflns_theta_max         24.000
_diffrn_reflns_theta_min         2.222
_diffrn_source                   'Incoatec Microfocus'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS-2014/5)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details
;
 Flack x determined using 2533 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       0.008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.314
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         9751
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.314
_refine_ls_R_factor_all          0.1484
_refine_ls_R_factor_gt           0.1179
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3162
_refine_ls_wR_factor_ref         0.3419
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                7199
_reflns_number_total             9751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b06228_si_002.cif
_cod_data_source_block           23
_cod_original_cell_volume        3278.1(14)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               4132770
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.995
_shelx_res_checksum              25265
_shelx_hkl_checksum              68608