Concise Syntheses of the Natural Products (+)-Sylvaticin and (+)-cis-Sylvaticin
Timothy J. Donohoe; Robert M. Harris; Oliver Williams; Gráinne C. Hargaden; Jeremy Burrows; Jeremy Parker; Journal of the American Chemical Society 131 (2009) 12854–12861; doi:10.1021/ja9049959

data_4104983
_publ_contact_author             'Timothy J. Donohoe'
_publ_contact_author_email       timothy.donohoe@chem.ox.ac.uk
_publ_section_title
;
 Concise Syntheses of the Natural Products (+)-Sylvaticin and
 (+)-cis-Sylvaticin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12854
_journal_page_last               12861
_journal_paper_doi               10.1021/ja9049959
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C14 H26 O4 '
_chemical_formula_sum            'C14 H26 O4'
_chemical_formula_weight         258.36
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   19.4191(2)
_cell_length_b                   19.4191(2)
_cell_length_c                   16.2612(2)
_cell_measurement_reflns_used    56006
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     6132.12(12)
_computing_cell_refinement
; 
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_data_collection
; 
KappaCCD software 'Collect' (Nonius, 2000) 
;
_computing_data_reduction
; 
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996) 
;
_computing_publication_material
; 
CRYSTALS (Watkin et al, 2001) 
;
_computing_structure_refinement
; 
CRYSTALS (Watkin et al, 2001) 
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
; 
Nonius KappaCCD 
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            56006
_diffrn_reflns_theta_full        27.480
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         5.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 Denzo/Scalepack (Otwinowski & Minor, 1996) 
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_thermal_history
; 
The material was crystallised at ambient temperature. A suitable crystal 
was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. 
;
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.0950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.049333
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 1.04 0.869 0.637 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0605
_refine_ls_wR_factor_gt          0.0468
_refine_ls_wR_factor_ref         0.0468
_reflns_limit_h_max              17
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                3090
_reflns_number_total             3980
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            ja9049959_si_001.cif
_cod_data_source_block           8
_cod_original_formula_sum        ' C14 H26 O4 '
_cod_database_code               4104983