A Short Diastereoselective Synthesis of the Putative Alkaloid Jamtine, Using a Tandem Pummerer/Mannich Cyclization Sequence
Albert Padwa; M. Diana Danca; Kenneth I. Hardcastle; Michael S. McClure; Journal of Organic Chemistry 68 (2003) 929–941; doi:10.1021/jo026471g

data_4022304
_publ_section_title
;
 A Short Diastereoselective Synthesis of the Putative Alkaloid Jamtine,
 Using a Tandem Pummerer/Mannich Cyclization Sequence
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              929
_journal_page_last               941
_journal_paper_doi               10.1021/jo026471g
_journal_volume                  68
_journal_year                    2003
_chemical_formula_sum            'C44 H58 N2 O10 S2'
_chemical_formula_weight         839.04
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   18.615(2)
_cell_length_b                   7.5693(8)
_cell_length_c                   28.852(3)
_cell_measurement_reflns_used    6957
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.512
_cell_measurement_theta_min      2.299
_cell_volume                     4065.3(7)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi & omega 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  0.0778
_diffrn_reflns_av_sigmaI/netI    0.0637
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30504
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.903002
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS2, Sheldrick, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         7118
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                5354
_reflns_number_total             7118
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo026471gsi20021107_031519.cif
_cod_data_source_block           k
_cod_database_code               4022304