First enantioselective total synthesis of (+)-(R)-pinnatolide using an asymmetric domino allylation reaction.
Tietze, Lutz F.; Wolfram, Thomas; Holstein, Julian J.; Dittrich, Birger; Organic letters 14 (2012) 4035–4037; doi:10.1021/ol301932d

data_1508353
_publ_section_title
;
 First enantioselective total synthesis of (+)-(R)-pinnatolide using an
 asymmetric domino allylation reaction.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4035
_journal_page_last               4037
_journal_paper_doi               10.1021/ol301932d
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H30 N2 O9'
_chemical_formula_sum            'C29 H30 N2 O9'
_chemical_formula_weight         550.55
_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                 111.5610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8209(2)
_cell_length_b                   27.0063(8)
_cell_length_c                   7.7986(2)
_cell_measurement_temperature    100(2)
_cell_volume                     1336.04(7)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2008)'
_computing_data_collection       'Apex2 (Bruker AXS, 2008)'
_computing_molecular_graphics    'shelXle (Huebschle et al, 2011)'
_computing_publication_material  'enCIFer 1.3, CCDC, 2008'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'INCOATEC multilayer optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            42964
_diffrn_reflns_theta_full        73.68
_diffrn_reflns_theta_max         73.68
_diffrn_reflns_theta_min         3.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS version 2008/2, multi-scan. (G. M. Sheldrick, 2008)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
Flack H D (1983), Acta Cryst. A39, 876-881 
Hooft W W, Straver L H, Spek A L, (2008), J. Appl Cryst. 41 , 96-103
Hooft W W, Straver L H, Spek A L, (2010), J. Appl Cryst. 43 , 665 -668
Parsons S, Wagner T, Presly O, Wood P A, Cooper R I (2012), 
J. Appl Cryst. 45, 417-429
;
_refine_ls_abs_structure_Flack   0.11(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5177
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0397P)^2^+0.7483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                5109
_reflns_number_total             5177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301932d_si_002.cif
_cod_data_source_block           tw112
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1508353
_computing_refinement_gui        'shelXle (Huebschle et al, 2011)'
_refine_ls_abs_structure_hooft   -0.01(3)
_refine_ls_abs_structure_parsons -0.02(3)