Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A, the Immunosuppressant (+)-SW-163A, and a JBIR-04 Diastereoisomer That Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A.
Manaviazar, Soraya; Nockemann, Peter; Hale, Karl J.; Organic letters 18 (2016) 2902–2905; doi:10.1021/acs.orglett.6b01235

data_1543360
_publ_section_title
;
 Total Synthesis of the GRP78-Downregulatory Macrolide (+)-Prunustatin A,
 the Immunosuppressant (+)-SW-163A, and a JBIR-04 Diastereoisomer That
 Confirms JBIR-04 Has Nonidentical Stereochemistry to (+)-Prunustatin A.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2902
_journal_page_last               2905
_journal_paper_doi               10.1021/acs.orglett.6b01235
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         '0.5(C21 H24 O4)'
_chemical_formula_sum            'C21 H24 O4'
_chemical_formula_weight         340.40
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.87215(15)
_cell_length_b                   17.2976(4)
_cell_length_c                   17.9057(5)
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.520
_cell_measurement_theta_min      0.550
_cell_volume                     1818.76(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku Supernova'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4496
_diffrn_reflns_theta_full        72.52
_diffrn_reflns_theta_max         72.52
_diffrn_reflns_theta_min         4.94
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.760
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                2948
_reflns_number_total             3079
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01235_si_004.cif
_cod_data_source_block           exp_71khsm1992
_cod_depositor_comments
'Adding full bibliography for 1543360--1543363.cif.'
_cod_original_cell_volume        1818.75(8)
_cod_database_code               1543360
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24),
 C25(H25)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'