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_1507160
_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 rm
_chemical_formula_moiety         'C12 H12 O4'
_chemical_formula_sum            'C12 H12 O4'
_chemical_formula_weight         220.22
_chemical_melting_point          125
_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                   5.5479(12)
_cell_length_b                   8.1165(3)
_cell_length_c                   25.0347(8)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    294
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0
_cell_volume                     1127.3(2)
_computing_cell_refinement       'Rigaku Diffractometer Controller'
_computing_data_collection       'Rigaku Diffractometer Controller'
_computing_data_reduction        'Rigaku Diffractometer Controller'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      294
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Quantum CCD1 on Rigaku AFC-7R'
_diffrn_measurement_method       PHIOMEGA
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9438
_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  1.5742
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor - Empirical Absorption Correction, 
Rigaku Corporation, Tokyo, Japan. 
;
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464.00
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.338
_refine_ls_extinction_coef       630(61)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.350
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1729
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'w = 1/[0.0007Fo^2^ + 7.0000\s(Fo^2^) + 0.0002]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0660
_reflns_number_gt                1729
_reflns_number_total             2486
_reflns_threshold_expression     F>2.0\s(F)
_cod_data_source_file            ol300185u_si_002.cif
_cod_data_source_block           Template
_cod_original_cell_volume        1127.3(3)
_cod_database_code               1507160