Asymmetric Synthesis of 4,8-Dihydroxyisochroman-1-one Polyketide Metabolites Using Chiral Hypervalent Iodine(III).
Fujita, Morifumi; Mori, Kazuhiro; Shimogaki, Mio; Sugimura, Takashi; Organic letters 14 (2012) 1294–1297; doi:10.1021/ol300185u

data_1507161
_publ_section_title
;
 Asymmetric Synthesis of 4,8-Dihydroxyisochroman-1-one Polyketide
 Metabolites Using Chiral Hypervalent Iodine(III).
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1294
_journal_page_last               1297
_journal_paper_doi               10.1021/ol300185u
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H9 Br O3'
_chemical_formula_sum            'C11 H9 Br O3'
_chemical_formula_weight         269.09
_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                   4.4554(16)
_cell_length_b                   11.569(4)
_cell_length_c                   20.465(7)
_cell_measurement_reflns_used    3228
_cell_measurement_temperature    294
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.99
_cell_volume                     1054.9(6)
_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    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      294
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4683
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.890
_exptl_absorpt_correction_T_max  0.678
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.430
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  899 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2346
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0727P)^2^+0.2286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1467
_reflns_number_gt                1603
_reflns_number_total             2346
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol300185u_si_003.cif
_cod_data_source_block           V111101a
_cod_original_cell_volume        1054.8(7)
_cod_database_code               1507161