Biomimetic Synthesis of Resorcylate Natural Products Utilizing Late Stage Aromatization: Concise Total Syntheses of the Marine Antifungal Agents 15G256ι and 15G256β
Ismael Navarro; Jean-François Basset; Séverine Hebbe; Sarah M. Major; Thomas Werner; Catherine Howsham; Jan Bräckow; Anthony G. M. Barrett; Journal of the American Chemical Society 130 (2008) 10293–10298; doi:10.1021/ja803445u

data_4108144
_publ_section_title
;
 Biomimetic Synthesis of Resorcylate Natural Products Utilizing Late Stage
 Aromatization: Concise Total Syntheses of the Marine Antifungal Agents
 15G256\i and 15G256\b
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10293
_journal_page_last               10298
_journal_paper_doi               10.1021/ja803445u
_journal_volume                  130
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H32 O12, C H4 O'
_chemical_formula_sum            'C29 H36 O13'
_chemical_formula_weight         592.58
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 93.8815(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   34.8354(4)
_cell_length_b                   8.90027(15)
_cell_length_c                   9.35124(8)
_cell_measurement_reflns_used    9655
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.2011
_cell_measurement_theta_min      2.5377
_cell_volume                     2892.65(6)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20622
_diffrn_reflns_theta_full        71.40
_diffrn_reflns_theta_max         71.40
_diffrn_reflns_theta_min         4.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) 
(compiled May  8 2007,13:10:02) 
empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 2519 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_coef       0.00023(4)
_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   0.915
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5507
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.914
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0283
_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^)+(0.0425P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0675
_reflns_number_gt                4320
_reflns_number_total             5507
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja803445u-file002.cif
_cod_data_source_block           Compound_2
_cod_database_code               4108144