Syntheses of Dihydroconduramines (±)-B-1, (±)-E-1, and (±)-F-1 via Diastereoselective Epoxidation of N-Protected 4-Aminocyclohex-2-en-1-ols.
Brennan, Méabh B; Csatayová, Kristína; Davies, Stephen G.; Fletcher, Ai M.; Green, William D.; Lee, James A.; Roberts, Paul M.; Russell, Angela J.; Thomson, James E.; The Journal of organic chemistry 80 (2015) 6609–6618; doi:10.1021/acs.joc.5b00716

data_4031122
_publ_section_title
;
 Syntheses of Dihydroconduramines (+-)-B-1, (+-)-E-1, and (+-)-F-1 via
 Diastereoselective Epoxidation of N-Protected 4-Aminocyclohex-2-en-1-ols.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6609
_journal_page_last               6618
_journal_paper_doi               10.1021/acs.joc.5b00716
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C20 H25 N1 O3'
_chemical_formula_sum            'C20 H25 N O3'
_chemical_formula_weight         327.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 98.764(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.6322(10)
_cell_length_b                   24.9350(11)
_cell_length_c                   9.3624(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     3837.5(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7990
_diffrn_reflns_theta_full        74.999
_diffrn_reflns_theta_max         81.521
_diffrn_reflns_theta_min         2.688
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  0.8861
_exptl_absorpt_correction_T_min  0.8755
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.03
_refine_diff_density_min         -0.97
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0928
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         7957
_refine_ls_number_restraints     867
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.0059263
_refine_ls_shift/su_mean         0.0002960
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 0.00P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2405
_refine_ls_wR_factor_gt          0.1925
_refine_ls_wR_factor_ref         0.2399
_reflns_limit_h_max              20
_reflns_limit_h_min              -20
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                4126
_reflns_number_total             7990
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.77
_oxford_diffrn_Wilson_scale      0.13
_oxford_refine_ls_r_factor_ref   0.1384
_oxford_refine_ls_scale          3.12(5)
_oxford_reflns_number_all        7960
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            jo5b00716_si_002.cif
_cod_data_source_block           39
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 4031119--4031122.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C20 H25 N1 O3'
_cod_database_code               4031122
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
SAME  C(114)  C(115)  C(116)  C(117)  C(118)  C(119)  C(120)  AND 
CONT  C(114)  C(115)  C(120)  C(119)  C(118)  C(117)  C(116)  AND 
CONT  C(214)  C(215)  C(216)  C(217)  C(218)  C(219)  C(220)  AND 
CONT  C(214)  C(215)  C(220)  C(219)  C(218)  C(217)  C(216) 
SIMU  0.01    C(114)  C(115)  C(116)  C(117)  C(118)  C(119)  C(120)  AND 
CONT  C(114)  C(115)  C(120)  C(119)  C(118)  C(117)  C(116)  AND 
CONT  C(214)  C(215)  C(216)  C(217)  C(218)  C(219)  C(220)  AND 
CONT  C(214)  C(215)  C(220)  C(219)  C(218)  C(217)  C(216) 
DELU  0.01    C(114)  C(115)  C(116)  C(117)  C(118)  C(119)  C(120)  AND 
CONT  C(114)  C(115)  C(120)  C(119)  C(118)  C(117)  C(116)  AND 
CONT  C(214)  C(215)  C(216)  C(217)  C(218)  C(219)  C(220)  AND 
CONT  C(214)  C(215)  C(220)  C(219)  C(218)  C(217)  C(216) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = O(1) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00200 = C(2) TO C(23) 
VIBR .0, 0.00500 = C(3) TO O(1) 
VIBR .0, 0.00500 = C(23) TO O(1) 
VIBR .0, 0.00500 = C(23) TO C(3) 
VIBR .0, 0.00200 = C(3) TO O(4) 
VIBR .0, 0.00200 = C(3) TO C(5) 
VIBR .0, 0.00500 = O(4) TO C(2) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00500 = C(5) TO O(4) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00200 = C(5) TO C(21) 
VIBR .0, 0.00500 = N(6) TO C(3) 
VIBR .0, 0.00500 = C(21) TO C(3) 
VIBR .0, 0.00500 = C(21) TO N(6) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00200 = N(6) TO C(14) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00500 = C(14) TO C(5) 
VIBR .0, 0.00500 = C(14) TO C(7) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00200 = C(8) TO C(13) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00500 = C(13) TO C(7) 
VIBR .0, 0.00500 = C(13) TO C(9) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO C(13) 
VIBR .0, 0.00500 = C(13) TO C(11) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(14) TO C(15) 
VIBR .0, 0.00500 = C(15) TO N(6) 
VIBR .0, 0.00200 = C(15) TO C(16) 
VIBR .0, 0.00200 = C(15) TO C(20) 
VIBR .0, 0.00500 = C(16) TO C(14) 
VIBR .0, 0.00500 = C(20) TO C(14) 
VIBR .0, 0.00500 = C(20) TO C(16) 
VIBR .0, 0.00200 = C(16) TO C(17) 
VIBR .0, 0.00500 = C(17) TO C(15) 
VIBR .0, 0.00200 = C(17) TO C(18) 
VIBR .0, 0.00500 = C(18) TO C(16) 
VIBR .0, 0.00200 = C(18) TO C(19) 
VIBR .0, 0.00500 = C(19) TO C(17) 
VIBR .0, 0.00200 = C(19) TO C(20) 
VIBR .0, 0.00500 = C(20) TO C(18) 
VIBR .0, 0.00500 = C(15) TO C(19) 
VIBR .0, 0.00200 = C(21) TO C(22) 
VIBR .0, 0.00500 = C(22) TO C(5) 
VIBR .0, 0.00200 = C(22) TO C(23) 
VIBR .0, 0.00500 = C(23) TO C(21) 
VIBR .0, 0.00200 = C(23) TO O(24) 
VIBR .0, 0.00500 = C(2) TO C(22) 
VIBR .0, 0.00500 = O(24) TO C(22) 
VIBR .0, 0.00500 = O(24) TO C(2) 
VIBR .0, 0.00200 = O(101) TO C(102) 
VIBR .0, 0.00200 = C(102) TO C(103) 
VIBR .0, 0.00200 = C(102) TO C(123) 
VIBR .0, 0.00500 = C(103) TO O(101) 
VIBR .0, 0.00500 = C(123) TO O(101) 
VIBR .0, 0.00500 = C(123) TO C(103) 
VIBR .0, 0.00200 = C(102) TO C(103) 
VIBR .0, 0.00200 = C(102) TO C(223) 
VIBR .0, 0.00500 = C(103) TO O(101) 
VIBR .0, 0.00500 = C(223) TO O(101) 
VIBR .0, 0.00500 = C(223) TO C(103) 
VIBR .0, 0.00200 = C(103) TO O(104) 
VIBR .0, 0.00200 = C(103) TO C(105) 
VIBR .0, 0.00500 = O(104) TO C(102) 
VIBR .0, 0.00500 = C(105) TO C(102) 
VIBR .0, 0.00500 = C(105) TO O(104) 
VIBR .0, 0.00200 = C(103) TO O(104) 
VIBR .0, 0.00200 = C(103) TO C(205) 
VIBR .0, 0.00500 = O(104) TO C(102) 
VIBR .0, 0.00500 = C(205) TO C(102) 
VIBR .0, 0.00500 = C(205) TO O(104) 
VIBR .0, 0.00200 = C(105) TO N(106) 
VIBR .0, 0.00200 = C(105) TO C(121) 
VIBR .0, 0.00500 = N(106) TO C(103) 
VIBR .0, 0.00500 = C(121) TO C(103) 
VIBR .0, 0.00500 = C(121) TO N(106) 
VIBR .0, 0.00200 = N(106) TO C(107) 
VIBR .0, 0.00200 = N(106) TO C(114) 
VIBR .0, 0.00500 = C(107) TO C(105) 
VIBR .0, 0.00500 = C(114) TO C(105) 
VIBR .0, 0.00500 = C(114) TO C(107) 
VIBR .0, 0.00200 = C(107) TO C(108) 
VIBR .0, 0.00500 = C(108) TO N(106) 
VIBR .0, 0.00200 = C(108) TO C(109) 
VIBR .0, 0.00200 = C(108) TO C(113) 
VIBR .0, 0.00500 = C(109) TO C(107) 
VIBR .0, 0.00500 = C(113) TO C(107) 
VIBR .0, 0.00500 = C(113) TO C(109) 
VIBR .0, 0.00200 = C(108) TO C(109) 
VIBR .0, 0.00200 = C(108) TO C(113) 
VIBR .0, 0.00200 = C(108) TO C(207) 
VIBR .0, 0.00500 = C(113) TO C(109) 
VIBR .0, 0.00500 = C(207) TO C(109) 
VIBR .0, 0.00500 = C(207) TO C(113) 
VIBR .0, 0.00200 = C(109) TO C(110) 
VIBR .0, 0.00500 = C(110) TO C(108) 
VIBR .0, 0.00200 = C(110) TO C(111) 
VIBR .0, 0.00500 = C(111) TO C(109) 
VIBR .0, 0.00200 = C(111) TO C(112) 
VIBR .0, 0.00500 = C(112) TO C(110) 
VIBR .0, 0.00200 = C(112) TO C(113) 
VIBR .0, 0.00500 = C(113) TO C(111) 
VIBR .0, 0.00500 = C(108) TO C(112) 
VIBR .0, 0.00200 = C(114) TO C(115) 
VIBR .0, 0.00500 = C(115) TO N(106) 
VIBR .0, 0.00200 = C(115) TO C(116) 
VIBR .0, 0.00200 = C(115) TO C(120) 
VIBR .0, 0.00500 = C(116) TO C(114) 
VIBR .0, 0.00500 = C(120) TO C(114) 
VIBR .0, 0.00500 = C(120) TO C(116) 
VIBR .0, 0.00200 = C(116) TO C(117) 
VIBR .0, 0.00500 = C(117) TO C(115) 
VIBR .0, 0.00200 = C(117) TO C(118) 
VIBR .0, 0.00500 = C(118) TO C(116) 
VIBR .0, 0.00200 = C(118) TO C(119) 
VIBR .0, 0.00500 = C(119) TO C(117) 
VIBR .0, 0.00200 = C(119) TO C(120) 
VIBR .0, 0.00500 = C(120) TO C(118) 
VIBR .0, 0.00500 = C(119) TO C(115) 
VIBR .0, 0.00200 = C(121) TO C(122) 
VIBR .0, 0.00500 = C(122) TO C(105) 
VIBR .0, 0.00200 = C(122) TO C(123) 
VIBR .0, 0.00500 = C(123) TO C(121) 
VIBR .0, 0.00200 = C(123) TO O(124) 
VIBR .0, 0.00500 = C(102) TO C(122) 
VIBR .0, 0.00500 = O(124) TO C(122) 
VIBR .0, 0.00500 = O(124) TO C(102) 
VIBR .0, 0.00200 = O(124) TO C(223) 
VIBR .0, 0.00200 = C(205) TO N(206) 
VIBR .0, 0.00200 = C(205) TO C(221) 
VIBR .0, 0.00500 = N(206) TO C(103) 
VIBR .0, 0.00500 = C(221) TO C(103) 
VIBR .0, 0.00500 = C(221) TO N(206) 
VIBR .0, 0.00200 = N(206) TO C(207) 
VIBR .0, 0.00200 = N(206) TO C(214) 
VIBR .0, 0.00500 = C(207) TO C(205) 
VIBR .0, 0.00500 = C(214) TO C(205) 
VIBR .0, 0.00500 = C(214) TO C(207) 
VIBR .0, 0.00500 = C(108) TO N(206) 
VIBR .0, 0.00200 = C(214) TO C(215) 
VIBR .0, 0.00500 = C(215) TO N(206) 
VIBR .0, 0.00200 = C(215) TO C(216) 
VIBR .0, 0.00200 = C(215) TO C(220) 
VIBR .0, 0.00500 = C(216) TO C(214) 
VIBR .0, 0.00500 = C(220) TO C(214) 
VIBR .0, 0.00500 = C(220) TO C(216) 
VIBR .0, 0.00200 = C(216) TO C(217) 
VIBR .0, 0.00500 = C(217) TO C(215) 
VIBR .0, 0.00200 = C(217) TO C(218) 
VIBR .0, 0.00500 = C(218) TO C(216) 
VIBR .0, 0.00200 = C(218) TO C(219) 
VIBR .0, 0.00500 = C(219) TO C(217) 
VIBR .0, 0.00200 = C(219) TO C(220) 
VIBR .0, 0.00500 = C(220) TO C(218) 
VIBR .0, 0.00500 = C(219) TO C(215) 
VIBR .0, 0.00200 = C(221) TO C(222) 
VIBR .0, 0.00500 = C(222) TO C(205) 
VIBR .0, 0.00200 = C(222) TO C(223) 
VIBR .0, 0.00500 = C(223) TO C(221) 
VIBR .0, 0.00500 = C(102) TO C(222) 
VIBR .0, 0.00500 = O(124) TO C(222) 
VIBR .0, 0.00500 = O(124) TO C(102) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.08000 = O(1) TO C(2) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(2) TO C(23) 
U(IJ) .0, 0.08000 = C(3) TO O(4) 
U(IJ) .0, 0.04000 = C(3) TO C(5) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = C(5) TO C(21) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = N(6) TO C(14) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(8) TO C(13) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO C(13) 
U(IJ) .0, 0.04000 = C(14) TO C(15) 
U(IJ) .0, 0.04000 = C(15) TO C(16) 
U(IJ) .0, 0.04000 = C(15) TO C(20) 
U(IJ) .0, 0.04000 = C(16) TO C(17) 
U(IJ) .0, 0.04000 = C(17) TO C(18) 
U(IJ) .0, 0.04000 = C(18) TO C(19) 
U(IJ) .0, 0.04000 = C(19) TO C(20) 
U(IJ) .0, 0.04000 = C(21) TO C(22) 
U(IJ) .0, 0.04000 = C(22) TO C(23) 
U(IJ) .0, 0.08000 = C(23) TO O(24) 
U(IJ) .0, 0.08000 = O(101) TO C(102) 
U(IJ) .0, 0.04000 = C(102) TO C(103) 
U(IJ) .0, 0.04000 = C(102) TO C(123) 
U(IJ) .0, 0.04000 = C(102) TO C(103) 
U(IJ) .0, 0.04000 = C(102) TO C(223) 
U(IJ) .0, 0.08000 = C(103) TO O(104) 
U(IJ) .0, 0.04000 = C(103) TO C(105) 
U(IJ) .0, 0.08000 = C(103) TO O(104) 
U(IJ) .0, 0.04000 = C(103) TO C(205) 
U(IJ) .0, 0.04000 = C(105) TO N(106) 
U(IJ) .0, 0.04000 = C(105) TO C(121) 
U(IJ) .0, 0.04000 = N(106) TO C(107) 
U(IJ) .0, 0.04000 = N(106) TO C(114) 
U(IJ) .0, 0.04000 = C(107) TO C(108) 
U(IJ) .0, 0.04000 = C(108) TO C(109) 
U(IJ) .0, 0.04000 = C(108) TO C(113) 
U(IJ) .0, 0.04000 = C(108) TO C(109) 
U(IJ) .0, 0.04000 = C(108) TO C(113) 
U(IJ) .0, 0.04000 = C(108) TO C(207) 
U(IJ) .0, 0.04000 = C(109) TO C(110) 
U(IJ) .0, 0.04000 = C(110) TO C(111) 
U(IJ) .0, 0.04000 = C(111) TO C(112) 
U(IJ) .0, 0.04000 = C(112) TO C(113) 
U(IJ) .0, 0.04000 = C(114) TO C(115) 
U(IJ) .0, 0.04000 = C(115) TO C(116) 
U(IJ) .0, 0.04000 = C(115) TO C(120) 
U(IJ) .0, 0.04000 = C(116) TO C(117) 
U(IJ) .0, 0.04000 = C(117) TO C(118) 
U(IJ) .0, 0.04000 = C(118) TO C(119) 
U(IJ) .0, 0.04000 = C(119) TO C(120) 
U(IJ) .0, 0.04000 = C(121) TO C(122) 
U(IJ) .0, 0.04000 = C(122) TO C(123) 
U(IJ) .0, 0.04000 = C(123) TO O(124) 
U(IJ) .0, 0.04000 = O(124) TO C(223) 
U(IJ) .0, 0.04000 = C(205) TO N(206) 
U(IJ) .0, 0.04000 = C(205) TO C(221) 
U(IJ) .0, 0.04000 = N(206) TO C(207) 
U(IJ) .0, 0.04000 = N(206) TO C(214) 
U(IJ) .0, 0.04000 = C(214) TO C(215) 
U(IJ) .0, 0.04000 = C(215) TO C(216) 
U(IJ) .0, 0.04000 = C(215) TO C(220) 
U(IJ) .0, 0.04000 = C(216) TO C(217) 
U(IJ) .0, 0.04000 = C(217) TO C(218) 
U(IJ) .0, 0.04000 = C(218) TO C(219) 
U(IJ) .0, 0.04000 = C(219) TO C(220) 
U(IJ) .0, 0.04000 = C(221) TO C(222) 
U(IJ) .0, 0.04000 = C(222) TO C(223) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;