Construction of the Tricyclic 5-7-6 Scaffold of Fungi-Derived Diterpenoids. Total Synthesis of (\±)-Heptemerone G and an Approach to Danishefsky's Intermediate for Guanacastepene A Synthesis
Karol Michalak; Michał Michalak; Jerzy Wicha; Journal of Organic Chemistry 75 (2010) 8337–8350; doi:10.1021/jo101758t

data_4025876
_publ_section_title
;
 Construction of the Tricyclic 5-7-6 Scaffold of Fungi-Derived
 Diterpenoids. Total Synthesis of (\+-)-Heptemerone G and an Approach to
 Danishefsky's Intermediate for Guanacastepene A Synthesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8337
_journal_page_last               8350
_journal_paper_doi               10.1021/jo101758t
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H30 Br O3'
_chemical_formula_sum            'C20 H30 Br O3'
_chemical_formula_weight         398.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_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           SHELXL-97
_cell_angle_alpha                91.009(3)
_cell_angle_beta                 93.458(3)
_cell_angle_gamma                102.291(3)
_cell_formula_units_Z            4
_cell_length_a                   10.7270(7)
_cell_length_b                   13.2190(6)
_cell_length_c                   14.0300(9)
_cell_measurement_reflns_used    5369
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.0
_cell_volume                     1939.4(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  Kappa/ccd
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9002
_diffrn_reflns_theta_full        21.97
_diffrn_reflns_theta_max         21.97
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    2.134
_exptl_absorpt_correction_T_max  0.5866
_exptl_absorpt_correction_T_min  0.4780
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   xabs2
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.088
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.258
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.258
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0777
_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^)+(0.0000P)^2^+29.8490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.1891
_reflns_number_gt                4074
_reflns_number_total             4711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101758t_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4025876