Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (-)-Huperzine N.
Bosch, Caroline; Fiser, Béla; Gómez-Bengoa, Enrique; Bradshaw, Ben; Bonjoch, Josep; Organic letters 17 (2015) 5084–5087; doi:10.1021/acs.orglett.5b02581

data_1555354
_publ_section_title
;
 Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction:
 Total Synthesis of (+)-Serratezomine E and Putative Structure of
 (-)-Huperzine N.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5084
_journal_page_last               5087
_journal_paper_doi               10.1021/acs.orglett.5b02581
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H32 N2 O'
_chemical_formula_sum            'C18 H32 N2 O'
_chemical_formula_weight         292.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.2870(2)
_cell_length_b                   9.4826(3)
_cell_length_c                   34.0330(12)
_cell_measurement_reflns_used    8046
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.15
_cell_measurement_theta_min      2.60
_cell_volume                     1706.23(10)
_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-97 (Sheldrick 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            12582
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.146
_diffrn_reflns_theta_min         2.597
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.537
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.11(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0457P)^2^+0.4500P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0943
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                3079
_reflns_number_total             3302
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02581_si_002.cif
_cod_data_source_block           cu_D43TB109_0m
_cod_database_code               1555354