Application of the intramolecular Yamamoto vinylogous aldol reaction to the synthesis of macrolides.
Abramite, Joseph A.; Sammakia, Tarek; Organic letters 9 (2007) 2103–2106; doi:10.1021/ol0704901

data_1505384
_publ_section_title
;
 Application of the intramolecular Yamamoto vinylogous aldol reaction to
 the synthesis of macrolides.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2103
_journal_page_last               2106
_journal_paper_doi               10.1021/ol0704901
_journal_volume                  9
_journal_year                    2007
_chemical_formula_moiety         'C21 H18 N2 O8'
_chemical_formula_sum            'C21 H18 N2 O8'
_chemical_formula_weight         426.37
_space_group_IT_number           2
_symmetry_cell_setting           i
_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_method           SHELXL-97
_cell_angle_alpha                103.3440(10)
_cell_angle_beta                 111.1300(10)
_cell_angle_gamma                99.1780(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4598(5)
_cell_length_b                   11.1436(7)
_cell_length_c                   11.9093(7)
_cell_measurement_reflns_used    4936
_cell_measurement_temperature    148(2)
_cell_measurement_theta_max      38.5165
_cell_measurement_theta_min      2.574
_cell_volume                     981.85(10)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELLXTL'
_computing_molecular_graphics    'Bruker XSCANS'
_computing_publication_material  'Bruker XSCANS'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      148(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\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  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6396
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3898
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0671P)^2^+0.2670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1613
_reflns_number_gt                3352
_reflns_number_total             3898
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol0704901si20070226_075120.cif
_cod_data_source_block           afs55
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505384