Organocatalytic Enantioselective Michael-Acetalization-Reduction-Nef Reaction for a One-Pot Entry to the Functionalized Aflatoxin System. Total Synthesis of (-)- Dihydroaflatoxin D2 and (-)- and (+)-Microminutinin.
Huang, Wei-Lun; Raja, Arun; Hong, Bor-Cherng; Lee, Gene-Hsiang; Organic letters 19 (2017) 3494–3497; doi:10.1021/acs.orglett.7b01473

data_1546305
_publ_section_title
;
 Organocatalytic Enantioselective Michael-Acetalization-Reduction-Nef
 Reaction for a One-Pot Entry to the Functionalized Aflatoxin System.
 Total Synthesis of (-)- Dihydroaflatoxin D2 and (-)- and
 (+)-Microminutinin.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3494
_journal_page_last               3497
_journal_paper_doi               10.1021/acs.orglett.7b01473
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H12 O4'
_chemical_formula_weight         208.21
_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   geom
_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                   7.0397(2)
_cell_length_b                   9.0581(3)
_cell_length_c                   15.2974(5)
_cell_measurement_reflns_used    6891
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.04
_cell_measurement_theta_min      5.68
_cell_volume                     975.46(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5299
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.890
_diffrn_reflns_theta_min         5.676
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
; 
 Flack x determined using 726 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_coef       0.0069(14)
_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   1.503
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.503
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0437P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1800
_reflns_number_total             1841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01473_si_004.cif
_cod_data_source_block           ic17676
_cod_depositor_comments
'Adding full bibliography for 1546305--1546306.cif.'
_cod_database_code               1546305
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.812
_shelx_estimated_absorpt_t_max   0.876
_shelx_res_checksum              78272
_shelx_hkl_checksum              23392