Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine. Establishment of the C-6 Hydroxyl Stereochemistry.
Rallapalli, Sundari K.; Namjoshi, Ojas A.; Tiruveedhula, V. V. N. Phani Babu; Deschamps, Jeffrey R.; Cook, James M.; The Journal of organic chemistry 79 (2014) 3776–3780; doi:10.1021/jo402692u

data_4029322
_publ_section_title
;
 Stereospecific Total Synthesis of the Indole Alkaloid Ervincidine.
 Establishment of the C-6 Hydroxyl Stereochemistry.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3776
_journal_page_last               3780
_journal_paper_doi               10.1021/jo402692u
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H22 N2 O2, 2(C H4 O)'
_chemical_formula_sum            'C21 H30 N2 O4'
_chemical_formula_weight         374.47
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3186(7)
_cell_length_b                   12.4731(10)
_cell_length_c                   19.1532(16)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.14
_cell_measurement_theta_min      2.67
_cell_volume                     1987.3(3)
_computing_cell_refinement       'Bruker APEX2 v2008.4-0 (Bruker, 2007)'
_computing_data_collection       'Bruker APEX2 v2008.4-0 (Bruker, 2007)'
_computing_data_reduction
;
Bruker SAINT v7.53A (Bruker, 2007), Bruker XPREP v2008/2 (Bruker, 2007)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.12 (Bruker, 2000b)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22977
_diffrn_reflns_theta_full        29.14
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisim
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.463
_exptl_crystal_size_mid          0.429
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         5326
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.2485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1055
_reflns_number_gt                5182
_reflns_number_total             5326
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo402692u_si_002.cif
_cod_data_source_block           cook107
_cod_depositor_comments
'Adding full bibliography for 4029322--4029323.cif.'
_cod_database_code               4029322