Total synthesis of (±)-epithuriferic acid methyl ester via Diels-Alder reaction.
Koprowski, Marek; Bałczewski, Piotr; Owsianik, Krzysztof; Różycka-Sokołowska, Ewa; Marciniak, Bernard; Organic & biomolecular chemistry 14 (2016) 1822–1830; doi:10.1039/c5ob02368h

data_7154871
_publ_section_title
;
 Total synthesis of (+-)-epithuriferic acid methyl ester via Diels-Alder
 reaction.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1822
_journal_page_last               1830
_journal_paper_doi               10.1039/c5ob02368h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C24 H27 O11 P'
_chemical_formula_sum            'C24 H27 O11 P'
_chemical_formula_weight         522.43
_chemical_name_systematic
'(rac)-(5R,6R,7S,8R)-5,8-Epoxynaphtho[2,3-d]-1,3-dioxole-6-carboxylic  acid, 5,6,7,8-tetrahydro-7-(dimethoxyphosphoryl)  -5-(3,4,5-trimethoxyphenyl)-, methyl ester'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-09-22 deposited with the CCDC.
2015-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.321(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9953(4)
_cell_length_b                   27.3594(8)
_cell_length_c                   9.1869(4)
_cell_measurement_reflns_used    4574
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      2.12
_cell_volume                     2574.50(18)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_data_collection
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies,V.1.171.36.20'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 16.1835
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire 3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4574
_diffrn_reflns_theta_full        25.12
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SCALE3 ABSPACK, CrysAlisPro, Agilent Technologies, V.1.171.36.20'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
?
;
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4574
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1375P)^2^+0.1878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1879
_reflns_number_gt                3921
_reflns_number_total             4574
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02368h2.cif
_cod_data_source_block           epoxy
_cod_depositor_comments
'Adding full bibliography for 7154870--7154871.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154871