An Expedient Formal Total Synthesis of (-)-Diazonamide A via a Powerful, Stereoselective O-Aryl to C-Aryl Migration To Form the C10 Quaternary Center
Chi-Ming Cheung; Frederick W. Goldberg; Philip Magnus; Claire J. Russell; Rachel Turnbull; Vince Lynch; Journal of the American Chemical Society 129 (2007) 12320–12327; doi:10.1021/ja0744448

data_4109983
_publ_section_title
;
 An Expedient Formal Total Synthesis of (-)-Diazonamide A via a Powerful,
 Stereoselective O-Aryl to C-Aryl Migration To Form the C10 Quaternary
 Center
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12320
_journal_page_last               12327
_journal_paper_doi               10.1021/ja0744448
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C33 H37 N4 O9 Br, C4 H8 O2'
_chemical_formula_sum            'C37 H45 Br N4 O11'
_chemical_formula_weight         801.68
_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                 93.780(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6274(3)
_cell_length_b                   11.7059(4)
_cell_length_c                   15.3407(6)
_cell_measurement_reflns_used    4495
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1904.28(11)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1079
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8487
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    1.144
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'DENZO and Scalepack (Otwinoski and Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       plates
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8487
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1407
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0290P)^2^+2.3083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1343
_reflns_number_gt                5101
_reflns_number_total             8487
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0744448si20070705_053703.cif
_cod_data_source_block           cjr257a
_cod_database_code               4109983