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_4030291
_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         'C19 H24 O7, H2 O1'
_chemical_formula_sum            'C19 H26 O8'
_chemical_formula_weight         382.41
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-03
_audit_creation_method           CRYSTALS_ver_14.43
_cell_angle_alpha                90
_cell_angle_beta                 105.1099(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8112(2)
_cell_length_b                   4.97960(10)
_cell_length_c                   23.1742(3)
_cell_measurement_reflns_used    4960
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     1872.91(5)
_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    'CAMERON (Watkin et al., 1996)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.034
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11280
_diffrn_reflns_theta_full        72.419
_diffrn_reflns_theta_max         72.419
_diffrn_reflns_theta_min         3.952
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.018
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 989 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.10(16)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0307
_refine_ls_shift/su_max          0.0003586
_refine_ls_shift/su_mean         0.0000275
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.60P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0771
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0771
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              6
_reflns_limit_k_min              -5
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                2944
_reflns_number_total             3061
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.23
_oxford_diffrn_Wilson_scale      0.03
_oxford_refine_ls_r_factor_ref   0.0321
_oxford_refine_ls_scale          5.81(10)
_oxford_reflns_number_all        3051
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'C:\Users\Hill Group\Desktop\Jas At 11:26 on '
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) H   (  13,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE O   (  21,X'S) H   ( 211,X'S) 
RIDE O   (  24,X'S) H   ( 241,X'S) 
RIDE O   (  25,X'S) H   ( 251,X'S) 
RIDE O   (  26,X'S) H   ( 261,X'S) 
RIDE O   ( 101,X'S) H   (1011,X'S) H   (1012,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            jo5024602_si_002.cif
_cod_data_source_block           BB.B167-Zeaenol
_cod_depositor_comments
'Adding full bibliography for 4030291--4030292.cif.'
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               4030291