Synthesis of Polysubstituted Furans Based on a Stepwise Sonogashira Coupling of (Z)-3-Iodoalk-2-en-1-ols with Terminal Propargylic Alcohols and Subsequent Au(I)- or Pd(II)-Catalyzed Cyclization-Aromatization via Elimination of H2O
Xiaobing Zhang; Zhan Lu; Chunling Fu; Shengming Ma; Journal of Organic Chemistry 75 (2010) 2589–2598; doi:10.1021/jo100146p

data_4025359
_publ_section_title
;
 Synthesis of Polysubstituted Furans Based on a Stepwise Sonogashira
 Coupling of (Z)-3-Iodoalk-2-en-1-ols with Terminal Propargylic Alcohols
 and Subsequent Au(I)- or Pd(II)-Catalyzed Cyclization-Aromatization via
 Elimination of H2O
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2589
_journal_page_last               2598
_journal_paper_doi               10.1021/jo100146p
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.40
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 113.9110(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8004(4)
_cell_length_b                   19.8870(9)
_cell_length_c                   10.0615(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1792.69(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20432
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.898479
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.242
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0583P)^2^+0.5227P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1241
_reflns_number_gt                2720
_reflns_number_total             3146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo100146p_si_001.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025359