Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi Macrocyclization Reaction.
Bolte, Benoit; Basutto, Jose A.; Bryan, Christopher S.; Garson, Mary J.; Banwell, Martin G.; Ward, Jas S.; The Journal of organic chemistry 80 (2014) 460–; doi:10.1021/jo5024602

data_4030292
_publ_section_title
;
 Modular Total Syntheses of the Marine-Derived Resorcylic Acid Lactones
 Cochliomycins A and B Using a Late-Stage Nozaki-Hiyama-Kishi
 Macrocyclization Reaction.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              460
_journal_paper_doi               10.1021/jo5024602
_journal_volume                  80
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_compound_source        'Research School of Chemistry'
_chemical_formula_moiety         'C22 H28 O7'
_chemical_formula_sum            'C22 H28 O7'
_chemical_formula_weight         404.46
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-14
_audit_creation_method           CRYSTALS_ver_14.43
_cell_angle_alpha                90
_cell_angle_beta                 94.3007(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.50360(10)
_cell_length_b                   26.1166(3)
_cell_length_c                   9.35440(10)
_cell_measurement_reflns_used    6556
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      5
_cell_volume                     2071.62(4)
_computing_cell_refinement       'CrysAlis PRO, (Agilent Technologies, 2013)'
_computing_data_collection       'SuperNova, (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlis PRO, (Agilent Technologies, 2013)'
_computing_molecular_graphics    'Ortep-3 for windows (Farrugia, 1997)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12967
_diffrn_reflns_theta_full        69.319
_diffrn_reflns_theta_max         72.207
_diffrn_reflns_theta_min         3.385
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.19
_refine_ls_abs_structure_details 'Flack (1983), 3307 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7408
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_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.0012209
_refine_ls_shift/su_mean         0.0000905
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.29P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0841
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0841
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              32
_reflns_limit_k_min              -31
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                7084
_reflns_number_total             7438
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.76
_oxford_diffrn_Wilson_scale      0.07
_oxford_refine_ls_r_factor_ref   0.0345
_oxford_refine_ls_scale          3.89(3)
_oxford_reflns_number_all        7408
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'C:\Users\Hill Group\Desktop\Jas At 18:36 on '
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
CONT H(221, X,Y,Z) 
CONT H(241, X,Y,Z) 
REM CONT H(1221, X,Y,Z) 
CONT H(1241, X,Y,Z) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM U(IJ) 0.0, 0.01 = C(112) TO C(119) 
REM U(IJ) 0.0, 0.01 = C(113) TO C(114) 
REM U(IJ) 0.0, 0.01 = C(116) TO C(117) 
REM U(IJ) 0.0, 0.01 = C(118) TO O(120) 
REM 
REM VIBR 0.0, 0.01 = C(112) TO C(119) 
REM VIBR 0.0, 0.01 = C(113) TO C(114) 
REM VIBR 0.0, 0.01 = C(116) TO C(117) 
REM VIBR 0.0, 0.01 = C(118) TO O(120) 
REM 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jo5024602_si_001.cif
_cod_data_source_block           BB.B165
_cod_depositor_comments
'Adding full bibliography for 4030291--4030292.cif.'
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4030292