Toward the development of a general chiral auxiliary. A total synthesis of (+)-tetronolide via a tandem ketene-trapping [4 + 2] cycloaddition strategy.
Boeckman, Jr, Robert K; Shao, Pengcheng; Wrobleski, Stephen T; Boehmler, Debra J; Heintzelman, Geoffrey R; Barbosa, Antonio J; Journal of the American Chemical Society 128 (2006) 10572–10588; doi:10.1021/ja0581346

data_4101249
_publ_section_title
;
 Toward the development of a general chiral auxiliary. A total
 synthesis of (+)-tetronolide via a tandem ketene-trapping [4 + 2]
 cycloaddition strategy.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10572
_journal_page_last               10588
_journal_paper_doi               10.1021/ja0581346
_journal_volume                  128
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C42 H58 O12'
_chemical_formula_sum            'C42 H58 O12'
_chemical_formula_weight         754.88
_chemical_name_common            boecp1
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2516(2)
_cell_length_b                   12.8193(2)
_cell_length_c                   24.8929(3)
_cell_measurement_reflns_used    6676
_cell_measurement_temperature    193(2)
_cell_volume                     3909.6(1)
_computing_cell_refinement       'XSCANS, Siemens'
_computing_data_collection       'XSCANS, Siemens'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Siemens SMART CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16931
_diffrn_reflns_theta_full        23.30
_diffrn_reflns_theta_max         23.30
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9673
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0524P)^2^+0.8104P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                3038
_reflns_number_total             3176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0581346si20060616_012803.cif
_cod_data_source_block           boecp1
_cod_database_code               4101249