Unified Strategy to Prostaglandins: Chemoenzymatic Total Synthesis of Cloprostenol, Bimatoprost, PGF2, Fluprostenol, and Travoprost Guided by Biocatalytic Retrosynthesis
Zhu, Kejie; Jiang, Meifen; Ye, Baijun; Zhang, Guo-Tai; Li, Weijian; Tang, Pei; Huang, Zedu; Chen, Fener; Chemical Science  (2021) –; doi:10.1039/D1SC03237B

data_1563859
_publ_section_title
;
 Unified Strategy to Prostaglandins: Chemoenzymatic Total Synthesis of
 Cloprostenol, Bimatoprost, PGF2&#xF061;, Fluprostenol, and Travoprost
 Guided by Biocatalytic Retrosynthesis
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03237B
_journal_year                    2021
_chemical_formula_sum            'C7 H6 Cl2 O2'
_chemical_formula_weight         193.02
_chemical_name_systematic
(3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2020-01-07 deposited with the CCDC.	2021-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6662(15)
_cell_length_b                   9.925(2)
_cell_length_c                   10.643(2)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      59.20
_cell_measurement_theta_min      3.61
_cell_volume                     809.8(3)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14618
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.961
_diffrn_reflns_theta_min         5.302
_exptl_absorpt_coefficient_mu    4.502
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 642 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.037(8)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0214P)^2^+0.1099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0594
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.700
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1621
_reflns_number_total             1748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03237b2.cif
_cod_data_source_block           ga_91109a_a
_cod_database_code               1563859
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.365
_shelx_estimated_absorpt_t_max   0.614
_shelx_res_checksum              46743
_shelx_hkl_checksum              52225