Total Synthesis of Uniflorine A, Casuarine, Australine, 3-epi-Australine, and 3,7-Di-epi-australine from a Common Precursor
Thunwadee Ritthiwigrom; Anthony C. Willis; Stephen G. Pyne; Journal of Organic Chemistry 75 (2010) 815–824; doi:10.1021/jo902355p

data_4025200
_publ_contact_author_address
;
Research School of Chemistry,
The Australian National University,
Canberra, A. C. T. 0200, Australia
;
_publ_contact_author_email       ' willis@rsc.anu.edu.au '
_publ_contact_author_fax         ' 61 2 6125 0750 '
_publ_contact_author_name        ' Anthony C. Willis '
_publ_contact_author_phone       ' 61 2 6125 4109 '
_publ_section_title
;
 Total Synthesis of Uniflorine A, Casuarine, Australine, 3-epi-Australine,
 and 3,7-Di-epi-australine from a Common Precursor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              815
_journal_page_last               824
_journal_paper_doi               10.1021/jo902355p
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_compound_source        ' from U Wollongong '
_chemical_formula_moiety         'C28 H39 N O4 Si'
_chemical_formula_sum            'C28 H39 N O4 Si'
_chemical_formula_weight         481.71
_space_group_IT_number           77
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4c'
_symmetry_space_group_name_H-M   'P 42'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-03-04
_audit_creation_method           CRYSTALS_ver_12.85
_audit_update_record
;
2009-03-04 - Report on C28 H39 N O4 Si
             by Anthony C. Willis
             for Thunwadee Ritthiwigrom and Steve Pyne

2009-03-04 - passes checkcif tests with few warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2693(6)
_cell_length_b                   19.2693(6)
_cell_length_c                   7.4979(1)
_cell_measurement_reflns_used    46292
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.6
_cell_volume                     2784.01(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28502
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.915
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details 'Flack (1983), 2214 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.00(11)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8724
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.000308
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0777
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0777
_reflns_limit_h_max              16
_reflns_limit_h_min              -15
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              -8
_reflns_number_gt                3762
_reflns_number_total             4859
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.66
_oxford_diffrn_Wilson_scale      2.88
_oxford_refine_ls_r_factor_ref   0.0506
_oxford_refine_ls_scale          0.6138(9)
_oxford_reflns_number_all        4859
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '3041200 wol0901'
_cod_data_source_file            jo902355p_si_002.cif
_cod_data_source_block           wol0901
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 42 '
_cod_database_code               4025200