Catalysis-Based and Protecting-Group-Free Total Syntheses of the Marine Oxylipins Hybridalactone and the Ecklonialactones A, B, and C
Volker Hickmann; Azusa Kondoh; Barbara Gabor; Manuel Alcarazo; Alois Fürstner; Journal of the American Chemical Society 133 (2011) 13471–13480; doi:10.1021/ja204027a

data_4106658
_publ_section_title
;
 Catalysis-Based and Protecting-Group-Free Total Syntheses of the Marine
 Oxylipins Hybridalactone and the Ecklonialactones A, B, and C
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13471
_journal_page_last               13480
_journal_paper_doi               10.1021/ja204027a
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration rmad
_chemical_compound_source        diethylether
_chemical_formula_moiety         'C16 H17 Cl N2 O6'
_chemical_formula_sum            'C16 H17 Cl N2 O6'
_chemical_formula_weight         368.77
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                HIV-HD-028-01
_audit_creation_date             2010-02-22
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4887(6)
_cell_length_b                   7.1507(3)
_cell_length_c                   14.5744(6)
_cell_measurement_reflns_used    9639
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.2287
_cell_measurement_theta_min      3.0925
_cell_volume                     1684.88(12)
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_collection       'PROTEUM2 (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_structure_refinement  'SHELXL-97 (G. M. Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (G. M. Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 66.67
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker AXS X8 Proteum'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'focusing multilayer optic'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19135
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    2.341
_exptl_absorpt_correction_T_max  0.8330
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.025(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0267
_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^)+(0.0288P)^2^+0.5722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                2469
_reflns_number_total             2577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja204027a_si_001.cif
_cod_data_source_block           6870sadabs
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4106658