Biomimetic Asymmetric Total Synthesis of (-)-Laurefucin via an Organoselenium-Mediated Intramolecular Hydroxyetherification
Byungsook Kim; Miseon Lee; Mi Jung Kim; Hyunjoo Lee; Sanghee Kim; Deukjoon Kim; Minseob Koh; Seung Bum Park; Kye Jung Shin; Journal of the American Chemical Society 130 (2008) 16807–16811; doi:10.1021/ja806304s

data_4108792
_publ_section_title
;
 Biomimetic Asymmetric Total Synthesis of (-)-Laurefucin via an
 Organoselenium-Mediated Intramolecular Hydroxyetherification
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16807
_journal_page_last               16811
_journal_paper_doi               10.1021/ja806304s
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C15 H21 Br O3 '
_chemical_formula_sum            'C15 H21 Br O3'
_chemical_formula_weight         329.23
_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                   8.3834(9)
_cell_length_b                   13.102(2)
_cell_length_c                   14.396(2)
_cell_measurement_reflns_used    6131
_cell_measurement_temperature    293.1
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1581.2(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.6.0'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9967
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.125
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15563
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_exptl_absorpt_coefficient_mu    2.609
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_description       block
_exptl_crystal_F_000             680.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3618
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0553P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1620
_reflns_number_gt                0
_reflns_number_total             15516
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja806304s_si_003.cif
_cod_data_source_block           '_Laurefucin5'
_cod_original_cell_volume        1581.2(3)
_cod_original_formula_sum        'C15 H21 Br O3 '
_cod_database_code               4108792