Simple, Efficient, and Modular Syntheses of Polyene Natural Products via Iterative Cross-Coupling
Suk Joong Lee; Kaitlyn C. Gray; James S. Paek; Martin D. Burke; Journal of the American Chemical Society 130 (2008) 466–468; doi:10.1021/ja078129x

data_4107302
_publ_section_title
;
 Simple, Efficient, and Modular Syntheses of Polyene Natural Products via
 Iterative Cross-Coupling
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              466
_journal_page_last               468
_journal_paper_doi               10.1021/ja078129x
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         '4(C7 H9 B Br N O4), 0.5(C4 H8 O2)'
_chemical_formula_sum            'C30 H40 B4 Br4 N4 O17'
_chemical_formula_weight         1091.54
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2006-04-27   text and data added, srw 
;
_cell_angle_alpha                64.761(3)
_cell_angle_beta                 80.814(4)
_cell_angle_gamma                84.864(4)
_cell_formula_units_Z            2
_cell_length_a                   11.427(3)
_cell_length_b                   13.496(3)
_cell_length_c                   15.460(4)
_cell_measurement_reflns_used    1001
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     2128.3(9)
_computing_cell_refinement       'SAINT V6.22 (Bruker, 2001)'
_computing_data_collection       'SMART V5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.22 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Siemens Platform/CCD'
_diffrn_measurement_method       'profile data from \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  g19kas
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23052
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  306
_diffrn_standards_number         341
_exptl_absorpt_coefficient_mu    3.855
_exptl_absorpt_correction_T_max  0.6444
_exptl_absorpt_correction_T_min  0.2828
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP (Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_description       tabular
_exptl_crystal_F_000             1088
_exptl_crystal_id                g19kas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.4 mm cryo-loop (Hampton Research) with the (-3 -2 -1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0032(2)
_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   1.002
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         7776
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+1.5262P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                5683
_reflns_number_total             7776
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja078129x-file005.cif
_cod_data_source_block           g19kas
_cod_original_cell_volume        2128.4(9)
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4107302