Enantioselective Total Syntheses of (-)-Palau'amine, (-)-Axinellamines, and (-)-Massadines
Ian B. Seiple; Shun Su; Ian S. Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A. Rodriguez; Daniel P. O'Malley; Tanja Gaich; Matthias Köck; Phil S. Baran; Journal of the American Chemical Society 133 (2011) 14710–14726; doi:10.1021/ja2047232

data_4106769
_publ_section_title
;
 Enantioselective Total Syntheses of (-)-Palau'amine, (-)-Axinellamines,
 and (-)-Massadines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14710
_journal_page_last               14726
_journal_paper_doi               10.1021/ja2047232
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C24 H41 N O6 Si'
_chemical_formula_weight         467.67
_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            20
_cell_length_a                   9.3124(2)
_cell_length_b                   21.0010(5)
_cell_length_c                   68.1246(15)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.79
_cell_measurement_theta_min      11.93
_cell_volume                     13323.1(5)
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       79
_diffrn_reflns_limit_l_min       -74
_diffrn_reflns_number            33787
_diffrn_reflns_theta_full        64.26
_diffrn_reflns_theta_max         64.26
_diffrn_reflns_theta_min         11.88
_exptl_absorpt_coefficient_mu    1.074
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             5080
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       0.00022(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1486
_refine_ls_number_reflns         19174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.889
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0740P)^2^+3.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                17320
_reflns_number_total             19174
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja2047232_si_003.cif
_cod_data_source_block           baran150
_cod_database_code               4106769