Discovery of a new PCC-mediated stereoselective oxidative spiroketalization process. An access to a new type of poly-THF spiroketal compound displaying anticancer activity
Piccialli, Vincenzo; Oliviero, Giorgia; Borbone, Nicola; Tuzi, Angela; Centore, Roberto; Hemminki, Akseli; Ugolini, Matteo; Cerullo, Vincenzo; Organic & Biomolecular Chemistry 7 (2009) 3036–; doi:10.1039/b906872d

data_7150699
_publ_section_title
;
 Discovery of a new PCC-mediated stereoselective oxidative
 spiroketalization process. An access to a new type of poly-THF
 spiroketal compound displaying anticancer activity
;
_journal_issue                   15
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3036
_journal_paper_doi               10.1039/b906872d
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C27 H42 O7'
_chemical_formula_sum            'C27 H42 O7'
_chemical_formula_weight         478.61
_chemical_name_common
'dioxaspiro(bicyclo(3.2.1)octane-2,2'-oxolane) derivative 1'
_chemical_name_systematic
;
dioxaspiro[bicyclo[3.2.1]octane-2,2'-oxolane]
derivative 1
;
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 91.450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2090(10)
_cell_length_b                   7.4940(10)
_cell_length_c                   25.505(5)
_cell_measurement_reflns_used    114
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.731
_cell_measurement_theta_min      3.177
_cell_volume                     2523.9(6)
_computing_cell_refinement
;
Dirax/lsq (Duisenberg et al., 2000)
;
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
EvalCCD (Duisenberg & Schreurs 1990-2000)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare at al, 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type
;
Bruker-Nonius 95mm CCD camera on \k-goniostat
;
_diffrn_measured_fraction_theta_full 0.855
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
CCD rotation images, thick slices
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_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    0.2385
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            18190
_diffrn_reflns_theta_full        27.81
_diffrn_reflns_theta_max         27.81
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker, 2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         18190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.2249
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0851P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2048
_reflns_number_gt                5205
_reflns_number_total             18190
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            b906872d.txt
_cod_data_source_block           picc2lt
_cod_database_code               7150699