Enantioselective Total Synthesis of the Mexicanolides: Khayasin, Proceranolide, and Mexicanolide
Jonathan M. Faber; Wilhelm A. Eger; Craig M. Williams; Journal of Organic Chemistry 77 (2012) 8913–8921; doi:10.1021/jo301182f

data_4027576
_publ_section_title
;
 Enantioselective Total Synthesis of the Mexicanolides: Khayasin,
 Proceranolide, and Mexicanolide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8913
_journal_page_last               8921
_journal_paper_doi               10.1021/jo301182f
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H20 Br1 N1 O,0.5(C4 H10 O)'
_chemical_formula_sum            'C19 H25 Br N O2.5'
_chemical_formula_weight         387.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0272(4)
_cell_length_b                   25.3773(12)
_cell_length_c                   9.6448(4)
_cell_measurement_reflns_used    3331
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0657
_cell_measurement_theta_min      2.9978
_cell_measurement_wavelength     0.71073
_cell_volume                     1963.80(16)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
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        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0696
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0863735
_diffrn_orient_matrix_UB_12      -0.0053408
_diffrn_orient_matrix_UB_13      0.0048066
_diffrn_orient_matrix_UB_21      0.0145531
_diffrn_orient_matrix_UB_22      -0.0267959
_diffrn_orient_matrix_UB_23      -0.0166712
_diffrn_orient_matrix_UB_31      0.0119749
_diffrn_orient_matrix_UB_32      -0.0058914
_diffrn_orient_matrix_UB_33      0.071498
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.191
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14488
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3
_exptl_absorpt_coefficient_mu    2.105
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.73192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
        empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.009(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.702
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         6917
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      0.702
_refine_ls_R_factor_all          0.135
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                2688
_reflns_number_total             6917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301182f_si_003.cif
_cod_data_source_block           577jf7
_cod_original_formula_sum        'C19 H25 Br N O2.50'
_cod_database_code               4027576