Formal Synthesis of (+)-Lasubine II and (-)-Subcosine II via Organocatalytic Michael Addition of a Ketone to an α-Nitrostyrene.
N V G, Moorthy; Dyapa, Rajendar; Pansare, Sunil V.; Organic letters 17 (2015) 5312–5315; doi:10.1021/acs.orglett.5b02677

data_1555367
_publ_section_title
;
 Formal Synthesis of (+)-Lasubine II and (-)-Subcosine II via
 Organocatalytic Michael Addition of a Ketone to an \a-Nitrostyrene.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5312
_journal_page_last               5315
_journal_paper_doi               10.1021/acs.orglett.5b02677
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H23 N O7'
_chemical_formula_sum            'C18 H23 N O7'
_chemical_formula_weight         365.37
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   10.20930(10)
_cell_length_b                   10.20930(10)
_cell_length_c                   30.4222(3)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      69.99
_cell_measurement_theta_min      5.00
_cell_volume                     2746.08(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART 6K CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            21010
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.063
_diffrn_reflns_theta_min         5.002
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  0.8772
_exptl_absorpt_correction_T_min  0.7529
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       rod
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.115
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
; 
 Flack x determined using 1353 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3170
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.2330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.837
_reflns_Friedel_fraction_max     0.827
_reflns_number_gt                3097
_reflns_number_total             3170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02677_si_002.cif
_cod_data_source_block           P65
_cod_original_cell_volume        2746.08(6)
_cod_database_code               1555367
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.833
_shelxl_version_number           2014/6
_shelx_res_checksum              24221
_shelx_hkl_checksum              93058