Remote stereocontrol in [3,3]-sigmatropic rearrangements: application to the total synthesis of the immunosuppressant mycestericin g.
Fairhurst, Nathan W. G.; Mahon, Mary F.; Munday, Rachel H.; Carbery, David R.; Organic letters 14 (2012) 756–759; doi:10.1021/ol203300k

data_1503592
_publ_section_title
;
 Remote stereocontrol in [3,3]-sigmatropic rearrangements: application to
 the total synthesis of the immunosuppressant mycestericin g.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              756
_journal_page_last               759
_journal_paper_doi               10.1021/ol203300k
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_sum            'C23.5 H33 Cl I N O6'
_chemical_formula_weight         587.86
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           169
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            12
_cell_length_a                   10.9498(2)
_cell_length_b                   10.9498(2)
_cell_length_c                   77.5761(19)
_cell_measurement_reflns_used    22508
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      67.3069
_cell_measurement_theta_min      3.4135
_cell_volume                     8055.1(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_diffrn_ambient_temperature      240(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       92
_diffrn_reflns_limit_l_min       -92
_diffrn_reflns_number            61225
_diffrn_reflns_theta_full        67.47
_diffrn_reflns_theta_max         67.47
_diffrn_reflns_theta_min         3.42
_exptl_absorpt_coefficient_mu    10.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3588
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         9351
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0498
_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^)+(0.0766P)^2^+7.9491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                8819
_reflns_number_total             9351
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203300k_si_001.cif
_cod_data_source_block           p10dc3
_cod_original_sg_symbol_H-M      P61
_cod_database_code               1503592