Biomimetic total synthesis of (±)-doitunggarcinone a and (+)-garcibracteatone.
Pepper, Henry P.; Tulip, Stephen J.; Nakano, Yuji; George, Jonathan H.; The Journal of organic chemistry 79 (2014) 2564–2573; doi:10.1021/jo500027k

data_4029181
_publ_section_title
;
 Biomimetic total synthesis of (+-)-doitunggarcinone a and
 (+)-garcibracteatone.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2564
_journal_page_last               2573
_journal_paper_doi               10.1021/jo500027k
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C33 H40 O4'
_chemical_formula_weight         500.65
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 104.066(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   21.9005(8)
_cell_length_b                   11.9505(4)
_cell_length_c                   21.1324(9)
_cell_measurement_temperature    173(2)
_cell_volume                     5365.0(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.884
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0525
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30429
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.35
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2160
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+4.2451P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1234
_reflns_number_gt                4518
_reflns_number_total             6518
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500027k_si_003.cif
_cod_data_source_block           e:\hp\hpx2\struct\final\hpx2
_cod_database_code               4029181