A Total Synthesis of Galbonolide B
Philip J. Parsons; Lewis Pennicott; James Eshelby; Matthias Goessman; Adrian Highton; Peter Hitchcock; Journal of Organic Chemistry 72 (2007) 9387–9390; doi:10.1021/jo701509r

data_4023028
_publ_section_title
;
 A Total Synthesis of Galbonolide B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9387
_journal_page_last               9390
_journal_paper_doi               10.1021/jo701509r
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H32 O5'
_chemical_formula_sum            'C21 H32 O5'
_chemical_formula_weight         364.47
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2006-12-05T19:10:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2709(4)
_cell_length_b                   17.9596(10)
_cell_length_c                   18.5642(12)
_cell_measurement_reflns_used    8101
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.986
_cell_measurement_theta_min      3.395
_cell_measurement_wavelength     0.71073
_cell_volume                     2090.8(2)
_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_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.268946E-1
_diffrn_orient_matrix_UB_12      -0.464527E-1
_diffrn_orient_matrix_UB_13      -0.282763E-1
_diffrn_orient_matrix_UB_21      0.104888
_diffrn_orient_matrix_UB_22      0.273891E-1
_diffrn_orient_matrix_UB_23      -0.307286E-1
_diffrn_orient_matrix_UB_31      0.117068
_diffrn_orient_matrix_UB_32      -0.138676E-1
_diffrn_orient_matrix_UB_33      0.340275E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2009
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8934
_diffrn_reflns_theta_full        23.07
_diffrn_reflns_theta_max         23.07
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_extinction_coef       0.019(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         1697
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0661
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1177P)^2^+0.6909P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.173
_refine_ls_wR_factor_ref         0.2048
_reflns_number_gt                1339
_reflns_number_total             1697
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701509r-File003.cif
_cod_data_source_block           dec206
_cod_database_code               4023028