Polyhydroxylated pyrrolizidine alkaloids from transannular iodoaminations: application to the asymmetric syntheses of (-)-hyacinthacine A1, (-)-7a-epi-hyacinthacine A1, (-)-hyacinthacine A2, and (-)-1-epi-alexine.
Brock, E. Anne; Davies, Stephen G.; Lee, James A.; Roberts, Paul M.; Thomson, James E.; Organic & biomolecular chemistry 11 (2013) 3187–3202; doi:10.1039/c3ob40205c

data_7152898
_publ_section_title
;
 Polyhydroxylated pyrrolizidine alkaloids from transannular
 iodoaminations: application to the asymmetric syntheses of
 (-)-hyacinthacine A1, (-)-7a-epi-hyacinthacine A1, (-)-hyacinthacine A2,
 and (-)-1-epi-alexine.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3187
_journal_page_last               3202
_journal_paper_doi               10.1039/c3ob40205c
_journal_volume                  11
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H15 N1 O3'
_chemical_formula_sum            'C8 H15 N O3'
_chemical_formula_weight         173.21
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9174(2)
_cell_length_b                   9.4363(3)
_cell_length_c                   14.0634(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     917.98(5)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2686
_diffrn_reflns_theta_full        72.938
_diffrn_reflns_theta_max         75.977
_diffrn_reflns_theta_min         5.646
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.0003045
_refine_ls_shift/su_mean         0.0000434
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.13P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0864
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0864
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                2443
_reflns_number_total             1119
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.99
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0382
_oxford_refine_ls_scale          8.9(3)
_oxford_reflns_number_all        2676
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c3ob40205c.txt
_cod_data_source_block           15
_cod_original_cell_volume        917.99(5)
_cod_original_formula_sum        'C8 H15 N1 O3'
_cod_database_code               7152898