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_7150700
_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         'C30 H50 O7'
_chemical_formula_sum            'C30 H50 O7'
_chemical_formula_weight         522.70
_chemical_name_common
'dioxaspiro(bicyclo(3.2.1)octane-2,2'-oxolane) derivative 2'
_chemical_name_systematic
;
dioxaspiro[bicyclo[3.2.1]octane-2,2'-oxolane]
derivative 2
;
_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                 111.634(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.162(4)
_cell_length_b                   8.489(9)
_cell_length_c                   24.593(4)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      16.869
_cell_measurement_theta_min      4.093
_cell_volume                     2942(3)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.2294
_diffrn_reflns_av_sigmaI/netI    0.2028
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22393
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2423
_refine_ls_R_factor_gt           0.0687
_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^)+(0.1066P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2574
_reflns_number_gt                1593
_reflns_number_total             5101
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            b906872d.txt
_cod_data_source_block           picc3lt
_cod_database_code               7150700