Total Synthesis of the Cytostatic Marine Natural Product Dibromophakellstatin via Three-Component Imidazolidinone Anellation
Michael Zöllinger; Peter Mayer; Thomas Lindel; Journal of Organic Chemistry 71 (2006) 9431–9439; doi:10.1021/jo061813u

data_4022167
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
Ludwig Maximilian University
Butenandtstrasse 5-13 (Haus F)
D-81377 Munich
Germany
;
_publ_contact_author_email       thomas.lindel@cup.uni-muenchen.de
_publ_contact_author_fax         '+49 089-2180-77734'
_publ_contact_author_name        'Thomas Lindel'
_publ_section_title
;
 Total Synthesis of the Cytostatic Marine Natural Product
 Dibromophakellstatin via Three-Component Imidazolidinone Anellation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9431
_journal_page_last               9439
_journal_paper_doi               10.1021/jo061813u
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C21 H24 Br2 N4 O8 S, 0.5(C H4 O)'
_chemical_formula_sum            'C21.5 H26 Br2 N4 O8.5 S'
_chemical_formula_weight         668.332
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_author_name               'Mayer, P.'
_audit_block_code                C21H24Br2N4O8S_MeOH_jn513_lindel
_audit_creation_date             20-Dec-05
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             06-Jul-06
_cell_angle_alpha                72.9238(8)
_cell_angle_beta                 80.5396(9)
_cell_angle_gamma                62.3585(13)
_cell_formula_units_Z            4
_cell_length_a                   13.2373(2)
_cell_length_b                   13.4037(2)
_cell_length_c                   17.8325(4)
_cell_measurement_reflns_used    10722
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     2677.84(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       phi/omega-scan
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0758291
_diffrn_orient_matrix_UB_12      -0.0021023
_diffrn_orient_matrix_UB_13      -0.0203417
_diffrn_orient_matrix_UB_21      -0.0360148
_diffrn_orient_matrix_UB_22      0.0869176
_diffrn_orient_matrix_UB_23      -0.0158592
_diffrn_orient_matrix_UB_31      0.0152669
_diffrn_orient_matrix_UB_32      0.0012514
_diffrn_orient_matrix_UB_33      0.0527249
_diffrn_radiation_collimation    0.25
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22281
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.15
_diffrn_source_current           45.00
_diffrn_source_power             2.250
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    3.159
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.65777(5)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1348
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         12054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0374P)^2^+3.3683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                8372
_reflns_number_total             12054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo061813urom20060901_080251.cif
_cod_original_formula_sum        'C21.50 H26 Br2 N4 O8.50 S'
_cod_database_code               4022167