Biomimetic Total Synthesis of (\±)-8-Oxoerymelanthine
Yuki Yoshida; Kunihiko Mohri; Kimiaki Isobe; Toshimasa Itoh; Keiko Yamamoto; Journal of Organic Chemistry 74 (2009) 6010–6015; doi:10.1021/jo9008645

data_4024751
_publ_contact_author_address
;
3-3165, Higashi-tamagawagakuen, Machida
Tokyo 194-8543
Japan
;
_publ_contact_author_email       yamamoto@ac.shoyaku.ac.jp
_publ_contact_author_name        'Yamamoto, Keiko'
_publ_section_title
;
Biomimetic Total Synthesis of (\+-)-8-Oxoerymelanthine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6010
_journal_page_last               6015
_journal_paper_doi               10.1021/jo9008645
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H25 N O10 S '
_chemical_formula_sum            'C22 H25 N O10 S'
_chemical_formula_weight         495.50
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_Int_Tables_number      148
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_audit_creation_date             2009-04-24
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_formula_units_Z            18
_cell_length_a                   34.5631(7)
_cell_length_b                   34.5631(7)
_cell_length_c                   10.2030(2)
_cell_measurement_reflns_used    15363
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.4
_cell_volume                     10555.6(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR2004
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku VariMax RAPID2 R'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.060
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            40183
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_exptl_absorpt_coefficient_mu    1.738
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.800
_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    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             4680.00
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.52
_refine_ls_extinction_coef       37(7)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4273
_refine_ls_R_factor_gt           0.0560
_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         0.1485
_reflns_number_gt                1666
_reflns_number_total             4273
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo9008645_si_001.cif
_cod_data_source_block           '_compound_11'
_cod_original_sg_symbol_H-M      'R -3:H'
_cod_original_formula_sum        'C22 H25 N O10 S '
_cod_database_code               4024751