Chemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes 8-Deoxydihydrotsugicoline and Radudiol.
Chang, Ee Ling; Bolte, Benoit; Lan, Ping; Willis, Anthony C.; Banwell, Martin G.; The Journal of organic chemistry 81 (2016) 2078–2086; doi:10.1021/acs.joc.6b00043

data_4036615
_publ_section_title
;
 Chemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes
 8-Deoxydihydrotsugicoline and Radudiol.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2078
_journal_page_last               2086
_journal_paper_doi               10.1021/acs.joc.6b00043
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C15 H26 O2'
_chemical_formula_sum            'C15 H26 O2'
_chemical_formula_weight         238.37
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             15-11-23
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-11-23 - Report on C15 H26 O2
            by Anthony C. Willis
            for   Benoit Bolte and Martin Banwell

2015-11-23 - passes checkcif tests with minor warnings

2015-12-11 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 99.7857(12)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   33.1997(4)
_cell_length_b                   9.6115(1)
_cell_length_c                   13.8952(2)
_cell_measurement_reflns_used    14099
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      3
_cell_volume                     4369.43(10)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement
;
CRYSTALS (Betteridge et al., 2003)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33684
_diffrn_reflns_theta_full        72.427
_diffrn_reflns_theta_max         72.427
_diffrn_reflns_theta_min         3.227
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Flack (1983), 3042 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.19(14)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         7638
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.0037395
_refine_ls_shift/su_mean         0.0001706
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.96P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0873
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0873
_reflns_limit_h_max              40
_reflns_limit_h_min              -40
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                7219
_reflns_number_total             7638
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.74
_oxford_diffrn_Wilson_scale      0.23
_oxford_refine_ls_r_factor_ref   0.0376
_oxford_refine_ls_scale          2.084(10)
_oxford_reflns_number_all        7638
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\ban1558BSN\Tony_ban1558BSN_da At 9:15 on '
_cod_data_source_file            jo6b00043_si_005.cif
_cod_data_source_block           Radudiol_17
_cod_original_sg_symbol_Hall     'C 2y '
_cod_original_sg_symbol_H-M      'C 1 2 1 '
_cod_database_code               4036615
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, O(1,U'S) UNTIL C(55) 
CONT C(50,OCC) C(53,OCC) C(54,OCC) 
CONT C(150,U'S,OCC) UNTIL C(154) 
CONT H(1,X'S) UNTIL H(69) 
CONT ENANTIO 
EQUIV C(50,OCC) C(53,OCC) C(54,OCC) 
CONT  C(150,OCC) C(153,OCC) C(154,OCC) 
WEIGHT -1  C(150,OCC) C(153,OCC) C(154,OCC) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) H   ( 333,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) H   ( 343,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) H   ( 353,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H(491,X'S) H(492,X'S) H(493,X'S) H(494,X'S) 
RIDE C   (  51,X'S) H(511,X'S) H(512,X'S) H(513,X'S) H(514,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) H   ( 523,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) H   ( 533,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) H   ( 543,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) H   ( 553,X'S) 
RIDE C   ( 153,X'S) H   (1531,X'S) H   (1532,X'S) H   (1533,X'S) 
RIDE C   ( 154,X'S) H   (1541,X'S) H   (1542,X'S) H   (1543,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.83, .02 = O(2) TO H(28), O(2) TO H(29) 
DIST 0.83, .02 = O(5) TO H(58), O(5) TO H(59) 
DIST 0.83, .02 = O(6) TO H(68), O(6) TO H(69) 
ANGLE 110, 2 = C(5) TO O(2) TO H(28), C(5) TO O(2) TO H(29) 
ANGLE 110, 2 = C(42) TO O(5) TO H(58), C(42) TO O(5) TO H(59) 
ANGLE 110, 2 = C(45) TO O(6) TO H(68), C(45) TO O(6) TO H(69) 
REM 
DIST 0.0, .02 = MEAN C(49) TO C(50), C(49) TO C(150) 
DIST 0.0, .02 = MEAN C(51) TO C(50), C(51) TO C(150) 
DIST 1.54, .02 = C(150) TO C(153), C(150) TO C(154) 
ANGLE 110 3 = C(153) TO C(150) TO C(154) 
REM 
U(IJ) 0.0, .01 = C(50) TO C(150) 
VIBR 0.0, .01 = C(53) TO C(153) 
VIBR 0.0, .01 = C(54) TO C(154) 
VIBR 0.0, .01 = C(50) TO C(153) 
VIBR 0.0, .01 = C(50) TO C(154) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;