Total synthesis of (-)-dihydrosporothriolide utilizing an indium-mediated reformatsky-claisen rearrangement.
Ishihara, Jun; Tsuru, Hiroaki; Hatakeyama, Susumi; The Journal of organic chemistry 79 (2014) 5908–5913; doi:10.1021/jo5008948

data_4029605
_publ_section_title
;
 Total synthesis of (-)-dihydrosporothriolide utilizing an indium-mediated
 reformatsky-claisen rearrangement.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5908
_journal_page_last               5913
_journal_paper_doi               10.1021/jo5008948
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C13 H20 O4'
_chemical_formula_sum            'C13 H20 O4'
_chemical_formula_weight         240.30
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.21(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.981(13)
_cell_length_b                   8.448(10)
_cell_length_c                   15.97(2)
_cell_measurement_reflns_used    2387
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.20
_cell_volume                     1311(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5444
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520.00
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1593
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0830
_reflns_number_gt                1341
_reflns_number_total             1593
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo5008948_si_001.cif
_cod_data_source_block           1350a
_cod_depositor_comments          'Adding full bibliography for 4029605.cif.'
_cod_database_code               4029605