First total synthesis of the 7-oxygenated carbazole alkaloids clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and the anti-HIV active siamenol using a highly efficient palladium-catalyzed approach.
Krahl, Micha P.; Jäger, Anne; Krause, Tilo; Knölker, Hans-Joachim; Organic & biomolecular chemistry 4 (2006) 3215–3219; doi:10.1039/b607792g

data_7151285
_publ_section_title
;
 First total synthesis of the 7-oxygenated carbazole alkaloids
 clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and
 the anti-HIV active siamenol using a highly efficient
 palladium-catalyzed approach.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3215
_journal_page_last               3219
_journal_paper_doi               10.1039/b607792g
_journal_volume                  4
_journal_year                    2006
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_melting_point          468
_chemical_name_common            'Clausine C (Clauszoline L)'
_chemical_name_systematic        'methyl 7-methoxy-9H-carbazole-3-carboxylate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                101.10(2)
_cell_angle_beta                 102.27(3)
_cell_angle_gamma                104.33(3)
_cell_formula_units_Z            2
_cell_length_a                   8.118(3)
_cell_length_b                   9.020(2)
_cell_length_c                   9.143(3)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      18.58
_cell_measurement_theta_min      4.80
_cell_volume                     612.2(4)
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997), SCHAKAL99 (Keller & Pierrard, 1999)'
_computing_publication_material
'WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2005)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       \f
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14687
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.7754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS version 2.10 (Sheldrick, Bruker AXS Inc.,2002)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0596P)^2^+0.2620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                1792
_reflns_number_total             2242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607792g.txt
_cod_data_source_block           an7
_cod_database_code               7151285