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_4033329
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1091(3)
_cell_length_b                   9.5133(4)
_cell_length_c                   22.6063(9)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.81
_cell_measurement_theta_min      3.91
_cell_volume                     1313.83(10)
_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 0.994
_diffrn_measured_fraction_theta_max 0.978
_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  0.0650
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10814
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        66.000
_diffrn_reflns_theta_max         69.806
_diffrn_reflns_theta_min         3.911
_diffrn_source                   'Bruker MicroStar microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.500
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       'Triangular plate'
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
; 
 Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0686
_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^)+(0.1638P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1811
_refine_ls_wR_factor_ref         0.1823
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2322
_reflns_number_total             2400
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02324_si_002.cif
_cod_data_source_block           q87f
_cod_depositor_comments
'Adding full bibliography for 4033329--4033330.cif.'
_cod_database_code               4033329
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.841
_shelx_estimated_absorpt_t_max   0.953
_shelx_res_checksum              75936
_shelx_hkl_checksum              12305