A formal [3+3]-annulation-based approach to pancratistatins: total synthesis of (±)-7-deoxy-pancratistatin and its 2-epi and 2,4-diepi analogues.
Nieto-García, Olaia; Lago-Santomé, Hugo; Cagide-Fagín, Fernando; Ortiz-Lara, Juan Carlos; Alonso, Ricardo; Organic & biomolecular chemistry 10 (2012) 825–834; doi:10.1039/c1ob06374j

data_7152135
_publ_section_title
;
 A formal [3+3]-annulation-based approach to pancratistatins: total
 synthesis of (+-)-7-deoxy-pancratistatin and its 2-epi and 2,4-diepi
 analogues.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              825
_journal_page_last               834
_journal_paper_doi               10.1039/c1ob06374j
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C14 H19 N O7'
_chemical_formula_sum            'C42 H57 N3 O21'
_chemical_formula_weight         939.91
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.713(2)
_cell_angle_beta                 99.524(2)
_cell_angle_gamma                99.393(2)
_cell_formula_units_Z            2
_cell_length_a                   13.063(2)
_cell_length_b                   13.707(2)
_cell_length_c                   13.950(2)
_cell_measurement_reflns_used    4837
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      2.36
_cell_volume                     2380.7(6)
_computing_cell_refinement       'BRUKER Smart'
_computing_data_collection       'BRUKER Smart'
_computing_data_reduction        'BRUKER Saint'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8754
_diffrn_reflns_theta_full        25.43
_diffrn_reflns_theta_max         25.43
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9771
_exptl_absorpt_correction_T_min  0.9559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.712
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     678
_refine_ls_number_reflns         8754
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      0.712
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0501
_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^)+(0.1378P)^2^+3.1409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1755
_reflns_number_gt                5268
_reflns_number_total             8754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06374j.txt
_cod_data_source_block           ra02og1n
_cod_original_cell_volume        2380.8(7)
_cod_database_code               7152135