An Ester Enolate-Claisen Rearrangement Route to Substituted 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of Lucentamycin A
Sujeewa Ranatunga; Jinsoo S. Kim; Ujjwal Pal; Juan R. Del Valle; Journal of Organic Chemistry 76 (2011) 8962–8976; doi:10.1021/jo201727g

data_4026716
_publ_section_title
;
 An Ester Enolate-Claisen Rearrangement Route to Substituted
 4-Alkylideneprolines. Studies toward a Definitive Structural Revision of
 Lucentamycin A
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8962
_journal_page_last               8976
_journal_paper_doi               10.1021/jo201727g
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_sum            'C28 H53 N6 O10.5'
_chemical_formula_weight         641.76
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.241(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.1660(14)
_cell_length_b                   7.5426(4)
_cell_length_c                   17.8290(9)
_cell_measurement_reflns_used    9219
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.41
_cell_volume                     3469.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33396
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.41
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker,SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       cut-prism
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+3.9916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                3807
_reflns_number_total             4642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201727g_si_001.cif
_cod_data_source_block           jdv5cm
_cod_original_formula_sum        'C28 H53 N6 O10.50'
_cod_database_code               4026716