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_4022886
_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_formula_moiety         'C26 H26 Cl4 O4 '
_chemical_formula_sum            'C26 H26 Cl4 O4'
_chemical_formula_weight         544.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                80.323(10)
_cell_angle_beta                 88.66(1)
_cell_angle_gamma                82.94(1)
_cell_formula_units_Z            2
_cell_length_a                   7.5703(8)
_cell_length_b                   7.9949(4)
_cell_length_c                   21.228(2)
_cell_measurement_reflns_used    3518
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.3
_cell_volume                     1256.9(2)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173.2
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9280
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.465
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3464
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.0007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_ref         0.0369
_reflns_number_gt                3464
_reflns_number_total             4583
_reflns_threshold_expression     F^2^>3.0\s(F^2^)
_cod_data_source_file            jo0700474si20070201_120050.cif
_cod_data_source_block           ri901
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C26 H26 Cl4 O4 '
_cod_database_code               4022886