Catalytic Asymmetric Synthesis of theendo-6-Aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Product fromLigusticum chuanxingvia 1,3-Dipolar Cycloaddition of a Formyl-Derived Carbonyl Ylide Using Rh2(S-TCPTTL)4
Naoyuki Shimada; Taiki Hanari; Yasunobu Kurosaki; Koji Takeda; Masahiro Anada; Hisanori Nambu; Motoo Shiro; Shunichi Hashimoto; Journal of Organic Chemistry 75 (2010) 6039–6042; doi:10.1021/jo101175b

data_4025644
_publ_section_title
;
 Catalytic Asymmetric Synthesis of
 theendo-6-Aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Product
 fromLigusticum chuanxingvia 1,3-Dipolar Cycloaddition of a Formyl-Derived
 Carbonyl Ylide Using Rh2(S-TCPTTL)4
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6039
_journal_page_last               6042
_journal_paper_doi               10.1021/jo101175b
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C19 H23 N2 O, C16 H17 O8 S'
_chemical_formula_sum            'C35 H40 N2 O9 S'
_chemical_formula_weight         664.77
_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                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.85647(12)
_cell_length_b                   14.9418(3)
_cell_length_c                   31.6799(7)
_cell_measurement_reflns_used    35155
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      4.1
_cell_volume                     3245.54(11)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93.1
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            38598
_diffrn_reflns_theta_full        68.25
_diffrn_reflns_theta_max         68.25
_exptl_absorpt_coefficient_mu    1.385
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.732
_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    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1408.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.29
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2484 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.016(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     427
_refine_ls_number_reflns         5836
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.0040
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0525P)^2^+0.5162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0959
_reflns_number_gt                5354
_reflns_number_total             5836
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo101175b_si_002.cif
_cod_data_source_block           '_sample-A'
_cod_original_cell_volume        3245.55(11)
_cod_original_formula_sum        'C35 H40 N2 O9 S '
_cod_database_code               4025644