Pd(II)-Mediated Alkynediol Spiroketalization: First Total Synthesis of (-)-Cephalosporolide E and (+)-Cephalosporolide F
C. V. Ramana; Sharad B. Suryawanshi; Rajesh G. Gonnade; Journal of Organic Chemistry 74 (2009) 2842–2845; doi:10.1021/jo802539z

data_4024429
_publ_section_title
;
Pd(II)-Mediated Alkynediol Spiroketalization: First Total Synthesis of
(-)-Cephalosporolide E and (+)-Cephalosporolide F
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2842
_journal_page_last               2845
_journal_paper_doi               10.1021/jo802539z
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H14 O5'
_chemical_formula_sum            'C10 H14 O5'
_chemical_formula_weight         214.21
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 110.889(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.258(8)
_cell_length_b                   8.970(10)
_cell_length_c                   8.410(10)
_cell_measurement_reflns_used    748
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.27
_cell_volume                     511.5(10)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'Phi and Omega Scan'
_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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2193
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.9420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(19)
_refine_ls_extinction_coef       0.18(3)
_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   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1621
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0731P)^2^+0.1088P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1460
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                1536
_reflns_number_total             1621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802539z_si_001.cif
_cod_data_source_block           sharad_19
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024429