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_1543363
_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         'C31 H43 N O11'
_chemical_formula_sum            'C31 H43 N O11'
_chemical_formula_weight         605.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.6917(6)
_cell_length_b                   14.8522(2)
_cell_length_c                   8.87923(16)
_cell_measurement_reflns_used    33607
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.72
_cell_measurement_theta_min      4.366
_cell_volume                     3651.87(11)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Supernova'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            33607
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.729
_diffrn_reflns_theta_min         4.366
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2007)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2916 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         7199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0702P)^2^+1.4659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                6897
_reflns_number_total             7199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01235_si_002.cif
_cod_data_source_block           sm19123_sq_sq
_cod_depositor_comments
'Adding full bibliography for 1543360--1543363.cif.'
_cod_original_cell_volume        3651.88(11)
_cod_database_code               1543363
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O00C)=Sof(C0)=Sof(C2)=Sof(H2a)=Sof(H2b)=Sof(H2c)=Sof(C3)=Sof(H3a)=
 Sof(H3b)=Sof(H3c)=Sof(C1AA)=Sof(H1Aa)=Sof(H1Ab)=Sof(H1Ac)=1-FVAR(1)
 Sof(O00B)=Sof(C014)=Sof(C016)=Sof(H01m)=Sof(H01n)=Sof(H01o)=Sof(C017)=
 Sof(H01p)=Sof(H01q)=Sof(H01r)=Sof(C018)=Sof(H01s)=Sof(H01t)=Sof(H01u)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C00I(H00I), C00N(H00N), C00O(H00O), C00Q(H00Q), C00T(H00T), C00W(H00W)
3.b Secondary CH2 refined with riding coordinates:
 C00M(H00a,H00b), C00P(H00d,H00e)
3.c Aromatic/amide H refined with riding coordinates:
 N00C(H00C), C00G(H00G), C00R(H00R), C00V(H00V), C00X(H00X), C00Z(H00Z)
3.d Idealised Me refined as rotating group:
 C00U(H00f,H00h,H00j), C00Y(H00k,H00l,H00m), C010(H01a,H01b,H01c), C011(H01d,
 H01e,H01f), C012(H01g,H01h,H01i), C013(H01j,H01k,H01l), C016(H01m,H01n,H01o),
 C017(H01p,H01q,H01r), C018(H01s,H01t,H01u), C2(H2a,H2b,H2c), C3(H3a,H3b,H3c),
 C1AA(H1Aa,H1Ab,H1Ac)
;
_shelx_res_checksum              52250
_shelx_hkl_checksum              44744
_shelx_fab_checksum              29606
_olex2_submission_special_instructions 'No special instructions were received'