Total Syntheses of Multiple Cladiellin Natural Products by Use of a Completely General Strategy
J. Stephen Clark; Raphaëlle Berger; Stewart T. Hayes; Hans Martin Senn; Louis J. Farrugia; Lynne H. Thomas; Angus J. Morrison; Luca Gobbi; Journal of Organic Chemistry 78 (2013) 673–696; doi:10.1021/jo302542h

data_4027872
_publ_section_title
;
 Total Syntheses of Multiple Cladiellin Natural Products by Use of a
 Completely General Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              673
_journal_page_last               696
_journal_paper_doi               10.1021/jo302542h
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H34 O4'
_chemical_formula_sum            'C20 H34 O4'
_chemical_formula_weight         338.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9388(6)
_cell_length_b                   8.1850(10)
_cell_length_c                   33.548(3)
_cell_measurement_reflns_used    4202
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55.24
_cell_measurement_theta_min      6.17
_cell_volume                     1905.3(3)
_computing_cell_refinement       'FSPROCESS CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_collection       'D*TREK CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_data_reduction        'FSPROCESS CrystalClear 1.4.0 (Rigaku, 2008)'
_computing_publication_material  'WINGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
'Rigaku R-AXIS RAPID IP Image Plate diffractometer'
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1051
_diffrn_reflns_av_unetI/netI     0.1092
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            13485
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.5809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear 1.4.0 (Rigaku, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.18
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.12
_refine_ls_R_factor_gt           0.0743
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+1.0562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                2926
_reflns_number_total             4356
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo302542h_si_001_3.cif
_cod_data_source_block           comp_9
_cod_database_code               4027872