Biomimetic Total Syntheses of Borreverine and Flinderole Alkaloids
Dattatraya H. Dethe; Rohan D. Erande; Alok Ranjan; Journal of Organic Chemistry 78 (2013) 10106–10120; doi:10.1021/jo4013833

data_4028659
_publ_contact_author_address
;
Department of Chemistry
Indian Institute of Technology Kanpur
Kanpur-208 016
India
;
_publ_contact_author_email       ddethe@iitk.ac.in
_publ_contact_author_name        'Dr. Dattatraya H. Dethe'
_publ_section_title
;
 Biomimetic Total Syntheses of Borreverine and Flinderole Alkaloids
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10106
_journal_page_last               10120
_journal_paper_doi               10.1021/jo4013833
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C28 H30 N2 O2'
_chemical_formula_sum            'C28 H30 N2 O2'
_chemical_formula_weight         426.54
_chemical_name_common            rohanester
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
_cell_angle_beta                 93.070(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.433(5)
_cell_length_b                   24.960(5)
_cell_length_c                   8.832(5)
_cell_measurement_reflns_used    3560
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.45
_cell_volume                     2296.6(18)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11910
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.24
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0631P)^2^+0.5793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                3327
_reflns_number_total             4070
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4013833_si_001.cif
_cod_data_source_block           rohanester
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028659