Application of the rodriguez-pattenden photo-ring contraction: total synthesis and configurational reassignment of 11-gorgiacerol and 11-epigorgiacerol.
Weinstabl, Harald; Gaich, Tanja; Mulzer, Johann; Organic letters 14 (2012) 2834–2837; doi:10.1021/ol301068h

data_1507741
_publ_section_title
;
 Application of the rodriguez-pattenden photo-ring contraction: total
 synthesis and configurational reassignment of 11-gorgiacerol and
 11-epigorgiacerol.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2834
_journal_page_last               2837
_journal_paper_doi               10.1021/ol301068h
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H24 O6'
_chemical_formula_sum            'C21 H24 O6'
_chemical_formula_weight         372.40
_chemical_name_common            11-Gorgiacerol
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7593(2)
_cell_length_b                   8.8488(3)
_cell_length_c                   36.9618(11)
_cell_measurement_reflns_used    9455
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.37
_cell_volume                     1883.68(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.2169
_diffrn_reflns_av_sigmaI/netI    0.0981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            57947
_diffrn_reflns_theta_full        30.11
_diffrn_reflns_theta_max         30.11
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_correction_T_min  0.9359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         5533
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                3766
_reflns_number_total             5533
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301068h_si_001.cif
_cod_data_source_block           HAWE029
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               1507741