Tremorgenic Indole Alkaloids. The Total Synthesis of (-)-Penitrem D
Amos B. Smith; Naoki Kanoh; Haruaki Ishiyama; Noriaki Minakawa; Jon D. Rainier; Richard A. Hartz; Young Shin Cho; Haifeng Cui; William H. Moser; Journal of the American Chemical Society 125 (2003) 8228–8237; doi:10.1021/ja034842k

data_4113881
_publ_contact_author_address
;
Department of Chemistry
University of Pennsylvania
3301 Spruce St.
Philadelphia, PA 19104
USA
;
_publ_contact_author_email       smithab@sas.upenn.edu
_publ_contact_author_name
;
Dr. Amos B. Smith III
;
_publ_contact_author_phone       1-215-898-4860
_publ_section_title
;
 Tremorgenic Indole Alkaloids. The Total Synthesis of (-)-Penitrem D
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_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8228
_journal_page_last               8237
_journal_paper_doi               10.1021/ja034842k
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C17 H26 O3'
_chemical_formula_weight         278.38
_chemical_melting_point          379(1)
_chemical_name_systematic
;
3-isopropenyl-6a-methyl-2,3,4a,5,6,6a,7,8,9,10-decahydro-benzo[f]chromene-2,
10a-diol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3925(14)
_cell_length_b                   23.112(2)
_cell_length_c                   6.4688(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1553.8(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare, 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measurement_device       'image plate area detector'
_diffrn_measurement_device_type  'Rigaku R-AXIS IIc'
_diffrn_measurement_method       'phi oscillations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8904
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_F_000             608
_exptl_crystal_preparation       benzene
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.72(279)
_refine_ls_extinction_coef       0.0289(53)
_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_all   1.130
_refine_ls_goodness_of_fit_obs   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_restrained_S_obs      1.170
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_obs          0.0821
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+0.8389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2098
_refine_ls_wR_factor_obs         0.2017
_reflns_number_observed          2421
_reflns_number_total             2791
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja034842ksi20030224_044947_4.cif
_cod_data_source_block           Cmpd(-)29
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+0.8389P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+0.8389P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4113881