Scalable Regioselective and Stereoselective Synthesis of Functionalized (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal Decanolides and Derivatives.
Sherwood, Alexander M.; Williamson, Samuel E.; Johnson, Stephanie N.; Yilmaz, Anil; Day, Victor W.; Prisinzano, Thomas E.; The Journal of organic chemistry 83 (2018) 980–992; doi:10.1021/acs.joc.7b02324

data_4033330
_publ_section_title
;
 Scalable Regioselective and Stereoselective Synthesis of Functionalized
 (E)-4-Iodobut-3-en-1-ols: Gram-Scale Total Synthesis of Fungal
 Decanolides and Derivatives.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              980
_journal_page_last               992
_journal_paper_doi               10.1021/acs.joc.7b02324
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.211(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   31.5874(9)
_cell_length_b                   5.49640(10)
_cell_length_c                   14.9670(4)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.74
_cell_measurement_theta_min      2.80
_cell_volume                     2598.51(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14624
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         69.865
_diffrn_reflns_theta_min         2.798
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       'Rectangular parallelepiped'
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.155
_refine_ls_abs_structure_details
; 
 Flack x determined using 1743 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.12(11)
_refine_ls_extinction_coef       0.0058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1616P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1952
_refine_ls_wR_factor_ref         0.1966
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.857
_reflns_number_gt                4342
_reflns_number_total             4462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02324_si_003.cif
_cod_data_source_block           q90f
_cod_depositor_comments
'Adding full bibliography for 4033329--4033330.cif.'
_cod_database_code               4033330
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.867
_shelx_estimated_absorpt_t_max   0.969
_shelx_res_checksum              97991
_shelx_hkl_checksum              17260