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_1568755
_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 ad
_chemical_formula_moiety         'C20 H21 N O4'
_chemical_formula_sum            'C20 H21 N O4'
_chemical_formula_weight         339.38
_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   geom
_audit_creation_date             2020-01-25
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003),
 SHELXL-2018/3, and manual edit
;
_audit_update_record
;
2023-02-05 deposited with the CCDC.	2023-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.038(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.105(2)
_cell_length_b                   8.9547(18)
_cell_length_c                   10.215(2)
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.73
_cell_measurement_theta_min      4.66
_cell_volume                     868.4(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_data_collection
'BIS V6.2.9/2018-03-16 & APEX3 v2018.7-2 (Bruker-AXS, 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.69
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15034
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.944
_diffrn_reflns_theta_min         4.607
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.8859.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       blade
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0415
_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^)+(0.0457P)^2^+0.3625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                3419
_reflns_number_total             3650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc00651d2.cif
_cod_data_source_block           v20001
_cod_depositor_comments
'Adding full bibliography for 1568754--1568762.cif.'
_cod_database_code               1568755
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.804
_refine_ls_abs_structure_hooft   0.14(10)
_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:
 C3(H3), C6(H6), C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C11(H11A,H11B), C13(H13A,H13B), C20(H20A,H20B)
2.c X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              50904
_olex2_submission_special_instructions 'No special instructions were received'