Total Synthesis of (+)-Cymbodiacetal: A Re-evaluation of the Biomimetic Route
Maliha Uroos; William Lewis; Alexander J. Blake; Christopher J. Hayes; Journal of Organic Chemistry 75 (2010) 8465–8470; doi:10.1021/jo101691n

data_4025868
_publ_section_title
;
 Total Synthesis of (+)-Cymbodiacetal: A Re-evaluation of the Biomimetic
 Route
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8465
_journal_page_last               8470
_journal_paper_doi               10.1021/jo101691n
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O4, C H Cl3'
_chemical_formula_sum            'C21 H31 Cl3 O4'
_chemical_formula_weight         453.81
_space_group_IT_number           1
_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           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                88.961(4)
_cell_angle_beta                 81.329(4)
_cell_angle_gamma                87.944(4)
_cell_formula_units_Z            2
_cell_length_a                   5.8952(2)
_cell_length_b                   10.8623(6)
_cell_length_c                   17.4689(8)
_cell_measurement_reflns_used    11963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.09
_cell_measurement_theta_min      4.07
_cell_volume                     1105.04(9)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_publication_material
'enCIFer (Allen et al., 2004; PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova single Cu source, Atlas detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_sigmaI/netI    0.015
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25223
_diffrn_reflns_theta_full        67.49
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         4.07
_exptl_absorpt_coefficient_mu    3.950
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.85
_refine_diff_density_min         -0.56
_refine_diff_density_rms         0.10
_refine_ls_abs_structure_details 'Flack, H.D. (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.41
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         25235
_refine_ls_number_restraints     161
_refine_ls_restrained_S_all      1.41
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0938
_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^)+(0.200P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.272
_refine_ls_wR_factor_ref         0.295
_reflns_number_gt                23662
_reflns_number_total             25235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101691n_si_002.cif
_cod_data_source_block           mucjhc
_cod_database_code               4025868