Development of a strategy for the asymmetric synthesis of polycyclic polyprenylated acylphloroglucinols via N-amino cyclic carbamate hydrazones: application to the total synthesis of (+)-clusianone.
Garnsey, Michelle R.; Lim, Daniel; Yost, Julianne M.; Coltart, Don M.; Organic letters 12 (2010) 5234–5237; doi:10.1021/ol1022728

data_1503295
_publ_section_title
;
 Development of a strategy for the asymmetric synthesis of polycyclic
 polyprenylated acylphloroglucinols via N-amino cyclic carbamate
 hydrazones: application to the total synthesis of (+)-clusianone.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5234
_journal_page_last               5237
_journal_paper_doi               10.1021/ol1022728
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C30 H46 N2 O2 S'
_chemical_formula_sum            'C30 H46 N2 O2 S'
_chemical_formula_weight         498.75
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.003(1)
_cell_angle_beta                 98.392(1)
_cell_angle_gamma                95.769(1)
_cell_formula_units_Z            2
_cell_length_a                   9.5949(2)
_cell_length_b                   12.2464(2)
_cell_length_c                   13.8441(3)
_cell_measurement_reflns_used    5796
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.7
_cell_measurement_theta_min      2.4
_cell_volume                     1470.58(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'CCD detector Smart6000'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17809
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         31.26
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.8093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     500
_refine_ls_number_reflns         8320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0648P)^2^+0.2768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                6496
_reflns_number_total             8320
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1022728_si_003.cif
_cod_data_source_block           sad
_cod_database_code               1503295