Total synthesis of (−)-ulapualide A, a novel tris-oxazole macrolide from marine nudibranchs, based on some biosynthesis speculation
Pattenden, Gerald; Ashweek, Neil J.; Baker-Glenn, Charles A. G.; Kempson, James; Walker, Gary M.; Yee, James G. K.; Organic & Biomolecular Chemistry 6 (2008) 1478–1497; doi:10.1039/b801036f

data_7150880
_publ_section_title
;
 Total synthesis of (&#x2212;)-ulapualide A, a novel tris-oxazole
 macrolide from marine nudibranchs, based on some biosynthesis
 speculation
;
_journal_issue                   8
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              1478
_journal_page_last               1497
_journal_paper_doi               10.1039/b801036f
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H54 O7 Si'
_chemical_formula_sum            'C33 H54 O7 Si'
_chemical_formula_weight         590.85
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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           'enCIFer editing of SHELXL97 CIF output'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.323(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.5372(5)
_cell_length_b                   11.0197(6)
_cell_length_c                   16.2672(9)
_cell_measurement_reflns_used    10224
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     1708.23(16)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2002)'
_computing_data_collection       'Bruker SMART version 5.624 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'enCIFer (Allen et al., 2004); PLATON'
_computing_structure_refinement  'SHELXL97-2 (Sheldrick, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART1000 CCD area detector'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.011
_diffrn_reflns_av_sigmaI/netI    0.014
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15706
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS version 2.05; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       sphenoid
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.47
_refine_diff_density_max         0.38
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         7597
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.058P)^2^+0.254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                7366
_reflns_number_total             7613
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b801036f.txt
_cod_data_source_block           bpsino
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7150880