Total Synthesis and Bioactivity of an Unnatural Enantiomer of Merrilactone A: Development of an Enantioselective Desymmetrization Strategy
Masayuki Inoue; Nayoung Lee; Satoshi Kasuya; Takaaki Sato; Masahiro Hirama; Miyako Moriyama; Yoshiyasu Fukuyama; Journal of Organic Chemistry 72 (2007) 3065–3075; doi:10.1021/jo0700474

data_4022887
_publ_section_title
;
 Total Synthesis and Bioactivity of an Unnatural Enantiomer
 of Merrilactone A: Development of an Enantioselective
 Desymmetrization Strategy
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3065
_journal_page_last               3075
_journal_paper_doi               10.1021/jo0700474
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C26 H26 Cl4 O4 '
_chemical_formula_sum            'C26 H26 Cl4 O4'
_chemical_formula_weight         544.30
_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'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.510(3)
_cell_length_b                   11.488(4)
_cell_length_c                   20.740(6)
_cell_measurement_reflns_used    8715
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     2504.1(13)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173.2
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.9920
_diffrn_measured_fraction_theta_max 0.9920
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26624
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.45
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2431 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5669
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0003Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0690
_reflns_number_gt                5281
_reflns_number_total             5669
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo0700474si20070201_120108.cif
_cod_data_source_block           '__sato520'
_cod_original_formula_sum        'C26 H26 Cl4 O4 '
_cod_database_code               4022887