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_4029182
_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           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 91.092(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2492(4)
_cell_length_b                   7.6175(2)
_cell_length_c                   23.1871(6)
_cell_measurement_temperature    173(2)
_cell_volume                     2692.94(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.911
_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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30824
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.04
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         6563
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0439P)^2^+1.0844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                4777
_reflns_number_total             6563
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500027k_si_001.cif
_cod_data_source_block           e:\hp\hpx4\struct\finished\hpx4
_cod_database_code               4029182