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_7154870
_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 H29 O11 P'
_chemical_formula_sum            'C24 H29 O11 P'
_chemical_formula_weight         524.44
_chemical_name_systematic
'(rac)-(5S,6S,7S,8R)-Naphtho[2,3-d]-1,3-dioxole-6-carboxylic acid, 5,6,7,8-tetrahydro-8-hydroxy-5-(3,4,5-trimethoxyphenyl) -7-( dimethoxyphosphoryl)-, methyl ester'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                79.723(5)
_cell_angle_beta                 74.590(6)
_cell_angle_gamma                72.609(7)
_cell_formula_units_Z            2
_cell_length_a                   10.0529(7)
_cell_length_b                   10.0781(8)
_cell_length_c                   13.2162(9)
_cell_measurement_reflns_used    18102
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      67.06
_cell_measurement_theta_min      4.62
_cell_volume                     1224.69(16)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Sapphire 3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18102
_diffrn_reflns_theta_full        67.06
_diffrn_reflns_theta_max         67.06
_diffrn_reflns_theta_min         4.62
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.535
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.432
_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    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0589
_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^)+(0.1469P)^2^+0.0965P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2115
_reflns_number_gt                3651
_reflns_number_total             4331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02368h2.cif
_cod_data_source_block           naphtho
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154870--7154871.cif.
;
_cod_original_cell_volume        1224.69(15)
_cod_database_code               7154870