Synthesis of (Z)-2-Acyl-2-enals via Retrocycloadditions of 5-Acyl-4-alkyl-4H-1,3-dioxins: Application in the Total Synthesis of the Cytotoxin (\±)-Euplotin A
Ronald A. Aungst; Raymond L. Funk; Journal of the American Chemical Society 123 (2001) 9455–9456; doi:10.1021/ja011470b

data_4115701
_publ_contact_author
;
   Prof. Raymond L. Funk
   Department of Chemistry
   The Pennsylvania State University
   152 Davey Laboratory
   University Park, PA  16802-6300  USA
;
_publ_contact_author_email       rlf@chem.psu.edu
_publ_contact_author_fax         1(814)?
_publ_contact_author_phone       1(814)8652057
_publ_section_title
;
 Synthesis of (Z)-2-Acyl-2-enals via Retrocycloadditions of
 5-Acyl-4-alkyl-4H-1,3-dioxins: Application in the Total Synthesis of the
 Cytotoxin (\+-)-Euplotin A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9455
_journal_page_last               9456
_journal_paper_doi               10.1021/ja011470b
_journal_volume                  123
_journal_year                    2001
_chemical_formula_moiety         'C14 H21 N O4 S'
_chemical_formula_sum            'C14 H21 N O4 S'
_chemical_formula_weight         299.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                89.942(2)
_cell_angle_beta                 87.724(2)
_cell_angle_gamma                74.343(2)
_cell_formula_units_Z            2
_cell_length_a                   5.6577(7)
_cell_length_b                   9.9499(12)
_cell_length_c                   13.5249(17)
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.59
_cell_volume                     732.50(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'Bruker SMART'
_diffrn_measurement_method       '\w scan frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0721
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5046
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0544
_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^)+(0.0730P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                2269
_reflns_number_total             3520
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja011470b.cif
_cod_data_source_block           n00002
_cod_database_code               4115701