General Strategy for Synthesis of C-19 Methyl-Substituted Sarpagine/Macroline/Ajmaline Indole Alkaloids Including Total Synthesis of 19(S),20(R)-Dihydroperaksine, 19(S),20(R)-Dihydroperaksine-17-al, and Peraksine.
Edwankar, Rahul V.; Edwankar, Chitra R.; Deschamps, Jeffrey R.; Cook, James M.; The Journal of organic chemistry 79 (2014) 10030–; doi:10.1021/jo5016163

data_4030052
_publ_section_title
;
 General Strategy for Synthesis of C-19 Methyl-Substituted
 Sarpagine/Macroline/Ajmaline Indole Alkaloids Including Total Synthesis
 of 19(S),20(R)-Dihydroperaksine, 19(S),20(R)-Dihydroperaksine-17-al, and
 Peraksine.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10030
_journal_paper_doi               10.1021/jo5016163
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H46 N2 O Sn'
_chemical_formula_sum            'C30 H46 N2 O Sn'
_chemical_formula_weight         569.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.165(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.3074(10)
_cell_length_b                   11.6936(17)
_cell_length_c                   17.175(2)
_cell_measurement_reflns_used    2664
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.40
_cell_volume                     1448.9(3)
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0662
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9936
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.8775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.032
_refine_diff_density_max         2.367
_refine_diff_density_min         -1.179
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5279
_refine_ls_number_restraints     150
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.067
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0704P)^2^+4.3456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1541
_reflns_number_gt                4434
_reflns_number_total             5279
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo5016163_si_004.cif
_cod_data_source_block           cook68z
_cod_depositor_comments
'Adding full bibliography for 4030052--4030055.cif.'
_cod_original_cell_volume        1448.9(4)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4030052