Synthetic Studies on Dicyclopenta[a,d]cyclooctane Terpenoids: Construction of the Core Structure of Fusicoccins and Ophiobolins on the Route Involving a Wagner-Meerwein Rearrangement
Michał Michalak; Karol Michalak; Zofia Urbanczyk-Lipkowska; Jerzy Wicha; Journal of Organic Chemistry 76 (2011) 7497–7509; doi:10.1021/jo201357p

data_4026589
_publ_section_title
;
 Synthetic Studies on Dicyclopenta[a,d]cyclooctane Terpenoids:
 Construction of the Core Structure of Fusicoccins and Ophiobolins on the
 Route Involving a Wagner-Meerwein Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7497
_journal_page_last               7509
_journal_paper_doi               10.1021/jo201357p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C27 H36 N2 O7'
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.219(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.836(4)
_cell_length_b                   8.7210(6)
_cell_length_c                   10.6844(11)
_cell_measurement_temperature    100(2)
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_computing_cell_refinement
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
;
_computing_data_collection
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CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
;
_computing_molecular_graphics    SHELXTL-97
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
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_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KM4CCD
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
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_diffrn_standards_decay_%        2
_diffrn_standards_number         '1 frame'
_exptl_absorpt_coefficient_mu    0.092
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_exptl_absorpt_correction_T_min  0.93
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;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle4 beta (release 11-11-2005 CrysAlis171 .NET)
(compiled Nov 11 2005,15:50:43)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
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_exptl_crystal_description       planar
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0022(5)
_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   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0390P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0693
_reflns_number_gt                3470
_reflns_number_total             4832
_reflns_threshold_expression     >2sigma(I)
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