Nitrone dipolar cycloaddition routes to piperidines and indolizidines. Part 9. Formal synthesis of (–)-pinidine and total synthesis of (–)-histrionicotoxin, (+)-histrionicotoxin and (–)-histrionicotoxin 235A
Davison, Edwin C.; Fox, Martin E.; Holmes, Andrew B.; Roughley, Stephen D.; Smith, Catherine J.; Williams, Geoffrey M.; Davies, John E.; Raithby, Paul R.; Adams, Joseph P.; Forbes, Ian T.; Press, Neil J.; Thompson, Mervyn J.; Journal of the Chemical Society, Perkin Transactions 1  (2002) 1494–1514; doi:10.1039/b200328g

data_7204352
_publ_section_title
;
 Nitrone dipolar cycloaddition routes to piperidines and indolizidines.
 Part 9. Formal synthesis of (--)-pinidine and total synthesis of
 (--)-histrionicotoxin, (+)-histrionicotoxin and (--)-histrionicotoxin 235A
;
_journal_issue                   12
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              1494
_journal_page_last               1514
_journal_paper_doi               10.1039/b200328g
_journal_year                    2002
_chemical_formula_moiety         'C12 H18 N2 O2'
_chemical_formula_sum            'C12 H18 N2 O2'
_chemical_formula_weight         222.28
_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                 93.60(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.949(2)
_cell_length_b                   14.011(4)
_cell_length_c                   12.055(3)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      10
_cell_volume                     1171.4(6)
_computing_cell_refinement       'R-Axis PROCESS (MSC, 1995)'
_computing_data_collection       'R-Axis PROCESS (MSC, 1995)'
_computing_data_reduction        'R-Axis PROCESS (MSC, 1995)'
_computing_molecular_graphics    'XP (Sheldrick, 1996)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'Rigaku R-AXIS IIc'
_diffrn_measurement_method       '/f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6718
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_coef       0.35(2)
_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   1.273
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3371
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.273
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0634P)^2^+0.2085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                3088
_reflns_number_total             3371
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            b200328g.txt
_cod_data_source_block           ah9705
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7204352