Formal Total Synthesis of (+)-C9-Deoxyomuralide from l-Leucine Using a Double Sacrificial Chirality Transfer Approach.
Bulman Page, Philip C.; Goodyear, Ross L.; Horton, Alexandra E.; Chan, Yohan; Karim, Rehana; O'Connell, Maria A; Hamilton, Christopher; Slawin, Alexandra M. Z.; Buckley, Benjamin R.; Allin, Steven M.; The Journal of organic chemistry 82 (2017) 12209–12223; doi:10.1021/acs.joc.7b02078

data_4033173
_publ_section_title
;
 Formal Total Synthesis of (+)-C9-Deoxyomuralide from l-Leucine Using a
 Double Sacrificial Chirality Transfer Approach.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12209
_journal_page_last               12223
_journal_paper_doi               10.1021/acs.joc.7b02078
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C11.25 H19.5 Cl0.5 N O4'
_chemical_formula_sum            'C11.25 H19.5 Cl0.5 N O4'
_chemical_formula_weight         250.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-30
_audit_creation_method           'by CrystalStructure 4.2'
_cell_angle_alpha                65.754(8)
_cell_angle_beta                 80.975(12)
_cell_angle_gamma                85.855(12)
_cell_formula_units_Z            4
_cell_length_a                   10.3698(15)
_cell_length_b                   11.4667(12)
_cell_length_c                   12.0264(11)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      1.90
_cell_volume                     1287.7(3)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14574
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.323
_diffrn_reflns_theta_min         1.876
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             538.00
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.57
_refine_diff_density_min         -1.09
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4660
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0616
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1187P)^2^+0.9654P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1936
_refine_ls_wR_factor_ref         0.2001
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3902
_reflns_number_total             4660
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo7b02078_si_002.cif
_cod_data_source_block           32
_cod_depositor_comments
'Adding full bibliography for 4033169--4033173.cif.'
_cod_database_code               4033173
_shelx_res_checksum              84198
_shelx_hkl_checksum              14158