Total Synthesis of the Lycorenine-Type Amaryllidaceae Alkaloid (\±)-Clivonine via a Biomimetic Ring-Switch from a Lycorine-Type Progenitor
Carles Giró Mañas; Victoria L. Paddock; Christian G. Bochet; Alan C. Spivey; Andrew J. P. White; Inderjit Mann; Wolfgang Oppolzer; Journal of the American Chemical Society 132 (2010) 5176–5178; doi:10.1021/ja910184j

data_4102265
_publ_section_title
;
 Total Synthesis of the Lycorenine-Type Amaryllidaceae Alkaloid
 (\+-)-Clivonine via a Biomimetic Ring-Switch from a Lycorine-Type
 Progenitor
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5176
_journal_page_last               5178
_journal_paper_doi               10.1021/ja910184j
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C17 H20 N O5, C H Cl3, Cl'
_chemical_formula_sum            'C18 H21 Cl4 N O5'
_chemical_formula_weight         473.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.729(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4338(2)
_cell_length_b                   22.7228(6)
_cell_length_c                   10.7268(3)
_cell_measurement_reflns_used    8174
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.1118
_cell_measurement_theta_min      2.5908
_cell_volume                     2037.00(9)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18968
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         32.18
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) 
(compiled May  6 2009,17:20:42) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablets
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6530
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0688P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1206
_reflns_number_gt                4519
_reflns_number_total             6530
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja910184j_si_003.cif
_cod_data_source_block           19
_cod_database_code               4102265