Toward a Formal Synthesis of Laureatin: Unexpected Rearrangements Involving Cyclic Ether Nucleophiles
Santosh Keshipeddy; Isamir Martínez; Bernard F. Castillo; Martha D. Morton; Amy R. Howell; Journal of Organic Chemistry 77 (2012) 7883–7890; doi:10.1021/jo301048z

data_4027496
_publ_section_title
;
 Toward a Formal Synthesis of Laureatin: Unexpected Rearrangements
 Involving Cyclic Ether Nucleophiles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7883
_journal_page_last               7890
_journal_paper_doi               10.1021/jo301048z
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'O6 N C16 H17'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                72.265(5)
_cell_angle_beta                 86.022(6)
_cell_angle_gamma                81.314(6)
_cell_formula_units_Z            4
_cell_length_a                   6.33117(11)
_cell_length_b                   16.0227(3)
_cell_length_c                   16.6694(12)
_cell_measurement_reflns_used    13329
_cell_measurement_temperature    93
_cell_measurement_theta_max      65.84
_cell_measurement_theta_min      6.78
_cell_volume                     1591.66(13)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 11.111
_diffrn_measured_fraction_theta_full 0.895
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17425
_diffrn_reflns_theta_full        65.84
_diffrn_reflns_theta_max         65.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       needle
_exptl_crystal_F_000             672.00
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.300
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     507
_refine_ls_number_reflns         4957
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.077
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1148P)^2^+0.6411P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1884
_reflns_number_gt                3938
_reflns_number_total             4957
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo301048z_si_002.cif
_cod_data_source_block           '_ah01'
_cod_original_formula_sum        'O6 N C16 H17'
_cod_database_code               4027496