Synthesis of 4-Methyldienoates Using a Vinylogous Horner-Wadsworth-Emmons Reagent. Application to the Synthesis of Trichostatic Acid
John T. Markiewicz; Douglas J. Schauer; Joakim Löfstedt; Steven J. Corden; Olaf Wiest; Paul Helquist; Journal of Organic Chemistry 75 (2010) 2061–2064; doi:10.1021/jo902422y

data_4025295
_publ_contact_author_address
;
Department of Chemistry and Biochemistry,
University of Notre Dame,
Notre Dame, IN 46556
USA
;
_publ_contact_author_email       phelquis@nd.edu
_publ_contact_author_fax         '+1 574 631 6652'
_publ_contact_author_name        'Paul Helquist'
_publ_contact_author_phone       '+1 574 631 7822'
_publ_section_title
;
 Synthesis of 4-Methyldienoates Using a Vinylogous Horner-Wadsworth-Emmons
 Reagent. Application to the Synthesis of Trichostatic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2061
_journal_page_last               2064
_journal_paper_doi               10.1021/jo902422y
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C23 H28 N2 O4'
_chemical_formula_sum            'C23 H28 N2 O4'
_chemical_formula_weight         396.47
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.888(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6684(5)
_cell_length_b                   7.4095(3)
_cell_length_c                   11.9159(5)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.7617
_cell_measurement_theta_min      3.7228
_cell_volume                     1026.47(7)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XCIF (Sheldrick, 2001)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2001)'
_computing_structure_solution    'XS (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART Apex CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15356
_diffrn_reflns_theta_full        69.49
_diffrn_reflns_theta_max         69.49
_diffrn_reflns_theta_min         3.72
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFCU2K-90'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  0.8536
_exptl_absorpt_correction_T_min  0.7739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2007). SADABS v.2007/4. University of G\"ottingen, Germany.
;
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(13)
_refine_ls_extinction_coef       0.0072(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0245
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0386P)^2^+0.1822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                3553
_reflns_number_total             3568
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902422y_si_003.cif
_cod_data_source_block           bcn344_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4025295