supplementary information - nature · supplementary information. doi: 10.1038/nchem.1971 si-1 ....
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NATURE CHEMISTRY | www.nature.com/naturechemistry 68
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-68
(R)-3d 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
O
Ph
t-BuO2C
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 69
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-69
Chiral HPLC traces: racemic
Chiral HPLC traces: enantioenriched
min10.5 11 11.5 12 12.5 13 13.5
mAU
0
100
200
300
400
500
600
700
DAD1 C, Sig=210,8 Ref=360,100 (AMADEU\AB445000.D)
11.
286
12.
148
min11 11.5 12 12.5 13 13.5
mAU
0
100
200
300
400
500
600
DAD1 C, Sig=210,8 Ref=360,100 (AMADEU\AB445003.D)
11.
353
12.
238
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 70
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-70
(R)-4a 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
S
Ph
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 71
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-71
Chiral HPLC traces: racemic
Chiral HPLC traces: enantioenriched
min0 10 20 30 40 50 60 70 80 90
mAU
0
0.5
1
1.5
2
2.5
DAD1 B, Sig=254,16 Ref=360,100 (MARTIN\MOC85-4.D)
Area: 633
.011
76
.57
6
Area: 660
.554
85
.77
2
min0 20 40 60 80 100
mAU
0
5
10
15
20
25
30
DAD1 B, Sig=254,16 Ref=360,100 (MARTIN\MOC91.D)
Area: 923
4.12
76
.37
5
Area: 210
.822
87
.10
5
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 72
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-72
(R)-5d 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
O
Ph
CO2t-Bu
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 73
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-73
Chiral SFC traces: racemic
Chiral SFC traces: enantioenriched
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 74
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-74
(R)-6a 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
N
Ph
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 75
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-75
Chiral SFC traces: racemic
Chiral SFC traces: enantioenriched
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 76
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-76
6j 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
TBSOH
H
H H
H
N
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 77
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-77
(R)-7a 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
OMeMeO
Ph
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 78
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-78
Chiral SFC traces: racemic
Chiral SFC traces: enantioenriched
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 79
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-79
7i 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
HOH
H
H H
H
OMeMeO
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 80
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-80
(S)-7k 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
Ph
OMe
MeO
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 81
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-81
Chiral HPLC traces: racemic
Chiral HPLC traces: enantioenriched
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 82
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-82
(S)-7l 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
Ph
OMe
MeO
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 83
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-83
Chiral HPLC traces: racemic
Chiral HPLC traces: enantioenriched
Chiral HPLC traces: enantioenriched + racemic
min0 2 4 6 8 10 12 14 16 18
mAU
0
50
100
150
200
250
300
350
400
DAD1 A, Sig=250,100 Ref=360,100 (MARTIN\MOD107R.D)
9.4
37
10.
963
min0 2 4 6 8 10 12 14 16 18
mAU
0
5
10
15
20
25
30
35
DAD1 A, Sig=250,100 Ref=360,100 (MARTIN\MOD165A1.D)
Area: 11
99.15
9.1
74
min0 2.5 5 7.5 10 12.5 15 17.5 20 22.5
mAU
0
100
200
300
400
500
DAD1 C, Sig=210,8 Ref=360,100 (MARTIN\MOC15000.D)
Area
: 814
4.78
9.4
69
Area
: 279
.214
10.
343
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 84
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-84
(R)-8a 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
Me2N
Ph
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 85
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-85
Chiral SFC traces: racemic
Chiral SFC traces: enantioenriched
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 86
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-86
8j 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
TBSOH
H
H H
H
NMe2
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 87
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-87
(R)-9a 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
MeO
Ph
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 88
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-88
Chiral SFC traces: racemic
Chiral SFC: enantioenriched
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 89
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-89
(R)-10a 1H NMR (400 MHz, CDCl3)
13C NMR (100 MHz, CDCl3)
Ph
© 2014 Macmillan Publishers Limited. All rights reserved.
NATURE CHEMISTRY | www.nature.com/naturechemistry 90
SUPPLEMENTARY INFORMATIONDOI: 10.1038/NCHEM.1971
SI-90
Chiral HPLC traces: racemic
Chiral HPLC traces: enantioenriched
© 2014 Macmillan Publishers Limited. All rights reserved.