Asymmetric and Highly Stereoselective Synthesis of the DEF-Ring Moiety of (-)-FR182877 and Its Derivative Inducing Mitotic Arrest.
Kobayakawa, Yu; Mori, Yusuke; Okajima, Hideki; Terada, Yasuhiko; Nakada, Masahisa; Organic letters 14 (2012) 2086–2089; doi:10.1021/ol300615w

data_1507615
_publ_section_title
;
 Asymmetric and Highly Stereoselective Synthesis of the DEF-Ring Moiety of
 (-)-FR182877 and Its Derivative Inducing Mitotic Arrest.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2086
_journal_page_last               2089
_journal_paper_doi               10.1021/ol300615w
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C12 H18 O4'
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.27
_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                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.3341(3)
_cell_length_b                   10.3949(4)
_cell_length_c                   14.8921(8)
_cell_measurement_reflns_used    15939
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.10
_cell_volume                     1135.33(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18463
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488.00
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.570
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                2412
_reflns_number_total             2618
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol300615w_si_002.cif
_cod_data_source_block           Kobayakawa-hydrate
_cod_database_code               1507615