Total synthesis of (-)-scabrolide A and (-)-yonarolide.
Hafeman, Nicholas J.; Loskot, Steven A.; Reimann, Christopher E.; Pritchett, Beau P.; Virgil, Scott C.; Stoltz, Brian M.; Chemical science 14 (2023) 4745–4758; doi:10.1039/d3sc00651d

data_1568761
_publ_section_title
;
 Total synthesis of (-)-scabrolide A and (-)-yonarolide.
;
_journal_issue                   18
_journal_name_full               'Chemical science'
_journal_page_first              4745
_journal_page_last               4758
_journal_paper_doi               10.1039/d3sc00651d
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration abs
_chemical_formula_sum            'C24 H30 O4.16 Si'
_chemical_formula_weight         413.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-02-05 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.237(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.267(3)
_cell_length_b                   9.667(3)
_cell_length_c                   15.436(4)
_cell_measurement_reflns_used    8747
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.34
_cell_measurement_theta_min      2.50
_cell_volume                     1070.3(6)
_computing_cell_refinement       'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker-AXS, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 KAPPA'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16781
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.501
_diffrn_reflns_theta_min         2.495
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             443
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
; 
 Flack x determined using 1982 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5995
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0392
_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^)+(0.0491P)^2^+0.1019P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                5235
_reflns_number_total             5995
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00651d2.cif
_cod_data_source_block           D19016
_cod_depositor_comments
'Adding full bibliography for 1568754--1568762.cif.'
_cod_original_cell_volume        1070.3(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1568761
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              25850