Total Synthesis of (+)-Ambruticin S: Probing the Pharmacophoric Subunit
Stephen Hanessian; Thilo Focken; Xueling Mi; Rupal Oza; Bin Chen; Dougal Ritson; Renaud Beaudegnies; Journal of Organic Chemistry 75 (2010) 5601–5618; doi:10.1021/jo100956v

data_4025598
_publ_section_title
;
 Total Synthesis of (+)-Ambruticin S: Probing the Pharmacophoric Subunit
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5601
_journal_page_last               5618
_journal_paper_doi               10.1021/jo100956v
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C10 H16 O3'
_chemical_formula_sum            'C10 H16 O3'
_chemical_formula_weight         184.23
_chemical_melting_point          '31-31 Celsius'
_chemical_name_common
'(1S, 2S, 3R)-tert-Butyl 2-formyl-3-methylcyclopropanecarboxylate'
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 115.814(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4645(4)
_cell_length_b                   9.8531(3)
_cell_length_c                   11.5532(5)
_cell_measurement_reflns_used    8533
_cell_measurement_temperature    170
_cell_measurement_theta_max      71.78
_cell_measurement_theta_min      4.69
_cell_volume                     1072.36(7)
_computing_cell_refinement       'SAINT V7.34A(Bruker AXS, 2007)'
_computing_data_collection       'APEX2  (Bruker AXS, 2008)'
_computing_data_reduction        'SAINT V7.34A(Bruker AXS, 2007)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.047
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13877
_diffrn_reflns_theta_full        72.37
_diffrn_reflns_theta_max         72.37
_diffrn_reflns_theta_min         4.25
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.9344
_exptl_absorpt_correction_T_min  0.8318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), 1730 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.07(15)
_refine_ls_extinction_coef       0.0403(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0526P)^2^+0.0961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                3854
_reflns_number_total             3985
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo100956v_si_003.cif
_cod_data_source_block           benit6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_angle_publ_flag' value 'Y' changed to 'y'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (40
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
the built-in table from CIF Core dictionary named 'cif_core.dic'
version 2.4.1 from 2010-06-29 (26 times).

'_geom_torsion_publ_flag'
value 'Y' changed to 'y' according to the built-in table from CIF
Core dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29
(40 times).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1072.35(7)
_cod_database_code               4025598