Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H.
Manjappa, Kiran B.; Syu, Jia-Ru; Yang, Ding-Yah; Organic letters 18 (2016) 332–335; doi:10.1021/acs.orglett.5b03524

data_1542369
_publ_section_title
;
 Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of
 Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of
 Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              332
_journal_page_last               335
_journal_paper_doi               10.1021/acs.orglett.5b03524
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C25 H15 N O2'
_chemical_formula_sum            'C25 H15 N O2'
_chemical_formula_weight         361.38
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.3899(8)
_cell_length_b                   6.7857(3)
_cell_length_c                   11.1470(5)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      26.24
_cell_measurement_theta_min      3.13
_cell_volume                     1769.22(13)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44862
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.007(2)
_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   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0956P)^2^+1.0967P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.1989
_reflns_number_gt                1584
_reflns_number_total             1971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03524_si_004.cif
_cod_data_source_block           bmk2270
_cod_database_code               1542369