Supplementary Figures
O OTBS
H nBu
3P
TBSOTf Et 3N
1) Ac2O, pyr HO
AcO
THF
O
O HO
70% 10
P1
1) LHMDS TBSCl, HMPA THF
2) NaBH 4 CeCl3•7H 2O MeOH
OH
TsNHNH2 EDCI, DMAP
OTBS HO
HO
84% P2
70% (2 steps)
HO 2C
AcO
CH 2Cl 2
P3
Ts N
H 2N
THF-AcOH-H2O
H 2N
Ts N
O 2) toluene, reflux
O
CH 2Cl 2
OTBS
OTBS
HO
HO
P4
MeNO 2
Ts
N
84%
37% HCHO nBu P 3 THF
P5
H
O
N H
SO3•pyr DMSO, Et 3N CH 2Cl 2
OH
Ts
N
Ts
N
OH
N H
O
MeNO 2
1) TMSI, HMDS CH 2Cl 2
N H
Ts
NO 2
H
O N
H
O
Ts
N
78% (2 steps)
NaBH 4 OH
N H
O
92% P8
2) Pd(OAc) 2 DMSO
O
P6
H TMG
9
H
O
quant.
8
O
OH
HO
68% (3 steps)
Hg(OTf) 2 (2 mol%)
78%
P9
MeOH
N H
O
P7
Ts
NO 2
H
O N
OH
N H
OH
49% (2 steps) 7
Supplementary Figure 1. Previous Synthesis of Compound 71
1
O Boc
N
H
11
Br 10
N H
OTBS
NHFmoc
OTBS
13
12
13 NOESY, 500 MHz, CDCl3
12 11
13
10
8.0
7.5
7.0
6.5
6.0
5.5
5.0
10
4.5
4.0
3.5
13
3.0
11
2.5
12
2.0
1.5
1.0
0.5
ppm
1
2
3
4
5
6
7
8 ppm
Supplementary Figure 2. NOESY spectrum of 13
2
N
10
MeO 2C Boc N H
H 11
14
13
12
OTBS
NHFmoc
OTBS
NOESY, 500 MHz, CDCl3
12 11
13
10
8.0
7.5
7.0
6.5
6.0
5.5
5.0
10
4.5
4.0
3.5
13
3.0
2.5
11
テ
2.0
12
1.5
1.0
0.5
ppm
1
2
3
4
5
6
7
8 ppm
Supplementary Figure 3. NOEY spectrum of 14
3
NOE
O BocHN
11 12
N O O
H
H
H
N
11
H OTBS
TBSO TBSO
H N
12
H O
H
TFAHN
N
HN
F 3C
OtBu
O
N
H
H
OTBS
O
H
19
19'
Supplementary Figure 4. NOE Analysis of Compound 19
Compound 19 in CDCl3
O
N N
O BocHN d, J = 14.5 Hz F 3C
HN O
13
H 11
OTBS 19
Natural Palau'amine in d6-DMSO (Scheuer)
dd, J = 11.5, 10.0 Hz (!)
H
d, J = 14.4 Hz OTBS
N
HN
dd, J = 11.5, 8.0 Hz (")
H H
O
N N
H 2N
N
H 2N HN
HO
13
H 11
t, J = 10.3 Hz (!)
H
dd, J = 10.1, 7.4 Hz (")
H H NH 2
Cl
palau'amine (1)
Supplementary Figure 5. Comparison of Coupling Constant of Compound 19 and Natural Palau’amine (1)
4
O MeO 2C Boc
②
!
MeO 2C
N
BocN
H
THF
N OTBS OTBS O
–78 to 0 ºC 10 min
18
O
N
LHMDS (3.05 eq)
NH
H
N F 3C
H N
H OTBS
N
F 3C O
OTBS
O BocHN
–78 ºC to rt 3h 74%
O
N
AcOH (1.0 eq)
F 3C
N H H OTBS
HN O
18B
OTBS 19
19
18
TLC (hexane/EtOAc = 3:1)
Supplementary Figure 6. TLC Analysis in the Conversion of Compound 18 to 19
5
THF2
THF2 Li2 Li2
C10
C10
Li1
N14 THF1
18A+2THF(I)
Li1
THF1
N14
18A+2THF(II)
Supplementary Figure 7. Optimized structures of 18A+2THF(I) and 18A+2THF(II).
Supplementary Figure 8.
Potential energy profiles for the cyclization reaction of
18A+2THF(I)→18B+2THF(I) and 18A+2THF(II)→18B+2THF(II).
The potential energies
(in kcal/mol) relative to 18A+2THF(I) are shown in parenthesis.
6
N N H H
OH
S1
NO 2
OTBS
400 MHz, CDCl3
9 8
2.1475 7 6
0.5495
0.9214 0.9871 5
0.7317 1.7971
4
0.6386 0.9147 1.0567
3
1.6319 5.1976 0.5431 2
0.6991
1
11.0613
0
6.9085 PPM
Supplementary Figure 9. 1H-NMR spectrum of S1
7
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\1-TBSCl-1H-1.ALS
O
Ts
1H,
10
2.0000
O
Ts
N N H
H
13 C, 125
OH S1
NO 2
OTBS
MHz, CDCl3
210 200 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
10
0
ppm
Supplementary Figure 10. 13C-NMR spectrum of S1
8
N N H H
OH
11
NHFmoc
OTBS
400 MHz, CDCl3
9 8
2.0723 2.0372 2.0901 7
0.9142
6
0.9571 0.9867 0.5580 1.2594 5
1.5876 0.8165 4
0.6994 1.6308 0.9502
1.6099 3
2.6852 0.9364 2
1.1567
1
10.4046
6.5225 0 PPM
Supplementary Figure 11. 1H-NMR spectrum of 11
9
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\2-SmI2-1H.ALS
O
H
1H,
10
2.0000
O
H
N N H
H
13 C, 125
OH 11
NHFmoc
OTBS
MHz, CDCl3
210 200 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
10
0
ppm
Supplementary Figure 12. 13C-NMR spectrum of 11
10
N N H H
OTBS
NHFmoc
OTBS
S2
400 MHz, CDCl3
9 8
2.0913 2.3753 7
0.8580
6
0.7725
0.6808 0.9810 0.8261 5
1.6612 0.8198 4
0.8096 1.7644 1.0645 0.9788 0.8157
3
2.1849 2
0.7998 1.3213
1
22.4627
0
13.2482 PPM
Supplementary Figure 13. 1H-NMR spectrum of S2
11
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\3-TBSOTf-1H.ALS
O
H
1H,
10
2.0000 2.0419
N N H
13 C,
H
190
180
OTBS
NHFmoc
OTBS S2
200
100 MHz, CDCl3
210
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
0
-10
PPM
12
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\3-TBSOTf-13C-2.ALS
O H
220
Supplementary Figure 14. 13C-NMR spectrum of S2
N N H H
12 OTBS
NHFmoc
OTBS
400 MHz, CDCl3
9 8
2.0159 2.0528 2.0971 7 6
0.9582
0.8603 3.0854 5
1.8035 0.9709 4
1.8377 0.9059 0.9553 0.9535 3
0.8590 0.9127 0.9596 2
1.0016
9.6103
1
8.7065 9.2699
2.9873 8.9608 0 PPM
Supplementary Figure 15. 1H-NMR spectrum of 12
13
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\4-Boc2O-1H.ALS
O
Boc
1H,
10
2.0000
O Boc
N
H
12
OTBS
NHFmoc
OTBS
100 MHz, CDCl3
N H
13 C,
210 200 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
10
0
ppm
Supplementary Figure 16. 13C-NMR spectrum of 12
14
N Br
N H
H
13 OTBS
NHFmoc
OTBS
400 MHz, CDCl3
9 8
2.0091 2.1375 2.2103 7 6
0.8832
1.8807 0.8810 5
0.9162 0.8313 1.8163 0.9391
4
0.8722 0.9360 1.0981 1.7258
3
0.7778 0.8091 2
1.1822 9.3550
1
18.8583
2.9571 3.0396 6.3663 0 PPM
Supplementary Figure 17. 1H-NMR spectrum of 13
15
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\5-NBS-1H-6.ALS
O
Boc
1H,
10
2.0000
N
Br
N H
H
13
180
OTBS
NHFmoc
OTBS
190
MHz, CDCl3
200
13 C, 100
210
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
0
-10
PPM
16
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\5-NBS-13C-5.ALS
O Boc
220
Supplementary Figure 18. 13C-NMR spectrum of 13
O Boc
N
H
11
Br 10
N H
OTBS
NHFmoc
OTBS
13
12
13 COSY, 500 MHz, CDCl3
12 11
13
テ
10
8.0
7.5
7.0
6.5
6.0
5.5
5.0
10
4.5
4.0
3.5
13
3.0
11
2.5
12
2.0
1.5
1.0
0.5
ppm
1
2
3
4
5
6
7
8 ppm
Supplementary Figure 19. COSY spectrum of 13
17
H
OTBS
NHFmoc
OTBS
8
2.1070 2.0687 7
0.8549 6
0.6954
2.4076 5
2.8404 1.9764 4
5.2919 1.0118 1.8919 3
0.8657
2
0.7807 0.7895 9.1526
1
20.8009
2.8880 3.0374
6.0032
0 PPM
Supplementary Figure 20. 1H-NMR spectrum of 14
18
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\6-K2CO3-1H.ALS
N
14
9
400 MHz, CDCl3
N H
MeO 2C
Boc
1H,
10
2.0000 1.9283
N
MeO 2C Boc N H
H
14
180
OTBS
NHFmoc
OTBS
190
MHz, CDCl3
200
13 C, 100
210
170
160
150
140
130
120
110
100
90
80
70
60
50
40
30
20
10
0
-10
PPM
19
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\6-K2CO3-13C-2.ALS
220
Supplementary Figure 21. 13C-NMR spectrum of 14
N
10
MeO 2C Boc N H
H 11
OTBS
NHFmoc
OTBS
7.5
7.0
6.5
6.0
5.5
5.0
10
4.5
4.0
3.5
13
3.0
11
2.5
2.0
12
1.5
1.0
0.5
ppm
1
2
3
4
5
6
7
8 ppm
20
13
12
14 COSY, 500 MHz, CDCl3
12 11
13
10
8.0
Supplementary Figure 22. COSY spectrum of 14
N
H
OTBS
NHFmoc
OTBS
8
2.1475 2.4743 7
0.4625
6
-0.0186
1.4633 5
0.4031
1.4885 0.6887 4
0.7553 0.8111 2.7776 3.1817 0.6955
3 2
1.5156 19.6665
1
22.4889
3.1918
10.3013
0 PPM
Supplementary Figure 23. 1H-NMR spectrum of 15
21
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\7-TFAA-1H 60C.ALS
N
O 15
9
400 MHz, CDCl3, 60 ºC
MeO 2C
Boc
F 3C
1H,
10
2.0000 1.9694
N O
H
15
OTBS
NHFmoc
OTBS
125 MHz, CDCl3, 60 ºC
N
MeO 2C Boc F 3C
13 C,
154 ppm
120
120.010 119.480
117.162 116.395 115
114.864
210 200 190 180 170 160 150 140 130 120 110 100
155
155.429 155.154 154.858 154.580
90
80
ppm
112.569
70
60
50
40
30
20
10
0
ppm
Supplementary Figure 24. 13C-NMR spectrum of 15
22
H O
NH
OTBS
9
H N
OTBS
8 7
1.0000 2.7322 0.9762
6
2.1123 5
0.8491
4
0.9148 0.9426 1.3351 2.7637 2.4430 1.0079
3 2
2.0034
13.9069
1
21.1569
3.0791 5.9963 3.3440 0 PPM
Supplementary Figure 25. 1H-NMR spectrum of 18
23
\\150.59.84.6\user\004BOT\takeuchi\palauamine data\8-pyrrole-1H 60C.ALS
N
MeO 2C
Boc N
O 18
400 MHz, CDCl3, 60 ºC
F 3C
1H,
10
0.8749
N N
MeO 2C Boc
O
H
18
O NH
OTBS
H N
OTBS
125 MHz, CDCl3, 60 ºC
F 3C
13 C,
156
154
210 200 190 180 170 160 150 140 130 120 110 100
158
156.136 155.434 155.140 154.842 154.545
90
ppm
80
120
119.438 70
118
60
30
ppm
112.537 40
114
114.838 50
116
117.138 116.492
20
10
0
ppm
Supplementary Figure 26. 13C-NMR spectrum of 18
24
F 3C N
O BocHN N
H
OTBS
19
O
9
H
500 MHz, CDCl3
HN
O
1H,
10
OTBS
8 7
0.97 0.90 0.95
0.99
6
1.00 0.97
4
2.00
5
1.02 1.01 1.02
1.06 1.01
3 0.99 0.99
ppm
5.82 3.03 3.14
1
9.20 9.33
2
1.04
Supplementary Figure 27. 1H-NMR spectrum of 19
25
F 3C N
O BocHN
HN
O
13 C, 125
N
H
OTBS
19
O
H OTBS
MHz, CDCl3
160 155 ppm
210 200 190 180 170 160 150 140 130 120 110 100
161.852 157.904 157.613 157.320 157.028 156.609 153.211
80 70
90
120.022 119.178 118.720 116.879 115
60
115.668 114.577 113.893
40
ppm
50
112.276
30 20 10 0 ppm
Supplementary Figure 28. 13C-NMR spectrum of 19
26
11 0.99
10 9 7
3.26 2.12 1.05 1.04 1.03
8
0.99
2.08
6 1.00 1.01
5
1.07 2.22 1.02 1.03 1.04
4
1.04 1.02
3
1.01
ppm
3.05 3.24 6.40
1
9.50 9.97
2
1.01
Supplementary Figure 29. 1H-NMR spectrum of 20
27
S
N N H
N H
O
OTBS 20
200
190
H OTBS
180
125 MHz, CDCl3
HN
HO CbzHN
F 3C O
13 C,
210
170
160
156.376 156.095 155.800 155.509
150
140
157 156
157.167
120
ppm
130
110
115.727 115.211
100
116
116.657
90
114.355
ppm
80
70
60
50
40
30
20
ppm
Supplementary Figure 30. 13C-NMR spectrum of 20
28
HO CbzHN
MeS
F 3C
N
N N
H
OTBS
21
O
9
H
500 MHz, CDCl3
HN
O
1H,
10
OTBS
1.00
8 5.36
7
1.01 1.03 1.00 1.06 1.04
6
2.07 1.12 1.96 1.04
5
1.05
4
1.06 1.09 1.06 1.04
3 1.03 1.06 3.13
2 1.08
ppm
3.26 3.65 6.25
1
10.01 9.77
Supplementary Figure 31. 1H-NMR spectrum of 21
29
HN
HO CbzHN MeS F 3C O
N N
N H
O
OTBS 21
H
MHz, CDCl3
OTBS
157
156
ppm
210 200 190 180 170 160 150 140 130 120 110 100
13 C, 125
156.401 156.114 155.828 155.540
90
80
120
119.285
70
116.981
60
115
50
ppm
114.677 114.525 114.140 112.372
40
30
20
10
0
ppm
Supplementary Figure 32. 13C-NMR spectrum of 21
30
Cbz
MeS
F 3C
1H,
N
HN
N
N
O
N
H
OTBS
22
O
9
H OTBS
500 MHz, CDCl3, 60 ºC
10 8 7 6 5 4 3
5.34 0.97 2.02 0.16 0.20 0.29 0.90 0.96 0.20 0.97 0.17 2.06 0.23 0.32 0.25 1.98 0.18 0.96 0.14 0.93 0.16 0.99 0.18 0.11 1.22 1.08 1.36 1.00 0.22 3.51 0.13 1.01 0.23
2
10.66 10.35
1
4.10 10.11
ppm
Supplementary Figure 33. 1H-NMR spectrum of 22
31
Cbz
MeS
F 3C
N
HN
N N
H
OTBS
22
O
H OTBS
MHz, CDCl3, 60 ºC
N
O
13 C, 125
156
155.444 155 ppm
210 200 190 180 170 160 150 140 130 120 110 100
156.433 156.346 156.267 156.139 156.029 155.735
90 80
118
70
116
60
114
119.161 118.430
50 ppm
40
116.858 115.347 114.671 114.558 114.126 113.614 113.521 112.355 111.846
30 20 10 0 ppm
Supplementary Figure 34. 13C-NMR spectrum of 22
32
Cbz N
S
N
N
H N
23 N
H
OTBS
9
O
H
500 MHz, C6D 6, 60 ºC
MeS
CbzHN
1H,
10 0.87
OTBS
8 7
1.18 2.39 3.27 4.78 2.76
2.12
6 0.74
5
1.00 1.33 3.45 1.29 1.06 1.26
4 1.00 1.17 1.01 1.14
3 0.81
3.23
2
9.30 8.70
1
5.18 2.88 2.97 5.85
ppm
Supplementary Figure 35. 1H-NMR spectrum of 23
33
O
N
Cbz
N
N
H
N
MeS
H
H N
CbzHN
OTBS
S
OTBS 23
Supplementary Figure 36. HRMS (ESI) spectrum of 23
34
Cbz
MeS
CbzHN
N N
N
N
N
H
OTBS
O
H OTBS
6 5
1.04 2.31 1.60 1.46 1.13 1.04 1.30 1.07 2.04
o-NO2BnHN
7
2.33 0.97
24
8
2.14
500 MHz, CDCl3, 60 ºC
9 1.19 1.20 1.38 1.35 7.73 2.73
1H,
10 0.92
4 1.18 1.16 1.12 1.10
3 1.04 3.44 1.14
2
10.34 9.63
1 ppm
7.33 3.02 4.49
Supplementary Figure 37. 1H-NMR spectrum of 24
35
Cbz MeS CbzHN
N
o-NO2BnHN
13 C, 125
N N N
24
N H
O
OTBS
H OTBS
MHz, CDCl3, 60 ºC
210 200 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
10
0
ppm
Supplementary Figure 38. 13C-NMR spectrum of 24
36
Cbz
MeS
CbzHN
N N
N
N
N
H
OH
O
H
8
OTIPS
500 MHz, CD3CN, 60 ºC
o-NO2BnHN
1H,
9 1.00
25
10 0.97
1.07 3.99 3.26 5.33
7
1.01 1.01
6
1.07 1.98
0.98 2.18
4
1.00 1.17 1.99 1.17
5
4.00 1.13 1.01
1.07
3
1.01 1.01
3.07
1
24.17
2
1.28
ppm
Supplementary Figure 39. 1H-NMR spectrum of 25
37
Cbz MeS CbzHN
N
o-NO2BnHN
13 C, 125
N N N
25
N H
OH
O
H OTIPS
MHz, CD 3CN, 60 ºC
210 200 190 180 170 160 150 140 130 120 110 100
90
80
70
60
50
40
30
20
10
0
ppm
Supplementary Figure 40. 13C-NMR spectrum of 25
38
N N
N
N
N HO
N
H
Cl
28
9
O
H
8
OTIPS
500 MHz, CD3CN, 60 ºC
Cbz
MeS
CbzHN
o-NO2Bn
1H,
10 1.16 13.58
7
1.88 1.00 0.96 1.22
6
1.04
6.47
5 0.71
4
3.40 0.88 2.28
3 1.00 3.82 0.82
2 1
23.65
ppm
Supplementary Figure 41. 1H-NMR spectrum of 28
39
7859::;76;!']2%%'#?'a7N4*44Y5444*44b 7477*K668N
U&%"@0C&'F12=Q"=/&
744 O4
7475*K6O99 747K*K6NK7
64 84
7478*K695K 54 4 :O4
747N*K6O5O
:O:*846K8 :ON
::4
::N
7444
744N
7474
747N
7454
748K*KN677
74KK*K8:47
745N*KO5:8
744N*844:N
745N
74K4
74KN
7484
748N
#MI 7859::;76;!']2%%'#?'a7N4*44Y5444*44b 7477*K668K
U&%"@0C&'F12=Q"=/&
744 O4
7475*K6O98 747K*K6N88
64 84
7478*K695N 54 4 :O4
747N*K6OK5
:O:*846K4 :ON
::4
744N*844O: ::N
7444
744N
74KK*K8:45
745N*KOK55 7474
747N
7454
745N
74K4
74KN
748K*KN65: 7484
#MI
!"#$#%&'"()*$+*,-&-*%(,#'.)/(*%($',,(0100234453 $KLM( 0114234453:0104234453 6,*&*+#((7-%(((7'8 9:0;(((((((1((((41 ?:05(((((((1(((((@ A-:;@((((((1(((((0 A:3;(((((((1(((((0 9":3B((((((1(((((0 9/'.C#(0 7',,(&*"#.'%)#(B211(++$ ?-&.*C#%(.D"#(%*&(D,#E( FGH(#ID-J(:0211:011211 $'8(.#,D"&,(011 $KL N/#*2(7',, G#"&'( O++$P (0100234453 (01002344B0 (((:121@ (01002344;@ ((((120B (0100234B43 ((((12Q> (0100234Q4; (((:020@ (0100234Q@; (((:023Q (010023454@ ((((02Q3 (010023455B ((((02>4 (
[email protected] ((((;2BQ (0100234>04 (((:;2Q1 (0100234>4B (((:320@ (0100234;5> ((((32>1 (010023Q1B1 (((:5213 (0100234;;4 ((((5203 (0100234;11 ((((523@ (010023Q1>> (((:52B0
O
N
Cbz
N
N
CbzHN
H
N N
o-NO2Bn
H
N
MeS
HO
OTIPS Cl 28
FGH( #ID-J2 (((352B (((352B (((;B2B (((3521 (((352B (((3>2B (((3>2B (((3121 (((3521 (((;>2B (((312B (((332B (((312B (((3B21 (((;>21
9*$+*,-&-*% 9 B> < B4 = 4 ? 4 9" A 9 B@ < B4 = Q ? 4 9" A9 B1 < 41 = > ? @ 9" A A9 41 < B@ = @ ? 3 9" A9 B4 < BB = Q ? @ A A9 41 < B0 = 4 ? @ A 9 B> < B0 = Q ? @ A9 B4 < B@ = > ? B 9" A 9 B@ < BQ = @ ? B A A9 BB < 41 = Q ? 4 9" A A9 B5 < B4 = @ ? @ 9" A 9 41 < B> = > ? ; A A9 B3 < B4 = > ? @ 9" A9 BQ < B3 = > ? Q A 9 BQ < 4; = @ ? 3 9" A A-
Supplementary Figure 42. HRMS (ESI) spectrum of 28
40
748N
Cbz
o-NO2BnHN
CbzHN
N N
N
HO
N
N
30
9
N
H
Cl
O
H
8
OTIPS
500 MHz, CD3CN, 60 ºC
o-NO2Bn
1H,
10 1.06 1.00 16.45
7
2.22 1.11 0.87 0.98
6
1.14
8.96
5 1.53
4
2.25 2.15
2.11
3 0.92
1.58
2
21.21
1 ppm
Supplementary Figure 43. 1H-NMR spectrum of 30
41
L"A&'+' 5M6M547N'5+K7+58'OE ?>@A32#&>A"%'#&AF)P'+' ,+-./"%0123-#&AF)
[email protected]!?:7442%-$>:G774:!8N*#&AF ?>@A32#&>A"%'Q>"%
[email protected]@'
[email protected])>S'BT20$#&>A'E">"H&#&>A',&>A&3S',3&"A0D&'U&@&"3/F'?>@A0A2A0)>S'G)VV"0P)'W>
[email protected] 785944:7;:(:$>'X7NY79 UZ+ 4*5NY4*59 Q[+ 5 (\+ K*97BN Z+ ]ZE!'^7S7_''`'$'B!?']2%%'#@'a7N4*44Y5444*44b 777N*85486
U&%"A0D&'Q12>P">/&
744 94
7776*85874 64
777;*857N5
84 7779*85569 54
77K;*84K6K 77K9*84695 7784*84NKK
777c*858N5
4 749N
74c4
74cN
7744
774N
7774
777N #MJ
7754
775N
77K4
77KN
7784
778N
785944:7;:(:$>'X79 UZ+ 4*K7 Q[+ 7 (\+ 9*K4BN Z+ ]ZE!'^7S7_''`'$'B!?']2%%'#@'a7N4*44Y5444*44b 777N*854;9
U&%"A0D&'Q12>P">/&
744 94
7776*8584; 64 777;*85799 84 7779*855c;
77K;*84K97 77K9*84665
54 777c*8587c 4 749N
74c4
74cN
7744
774N
7774
777N #MJ
7754
7784*848;c 775N
77K4
77KN
7784
778N
785944:7;:(:$>'X54 UZ+ 4*K8 Q[+ 7 (\+ 7*45B6 Z+ ]ZE!'^7S7_''`'$'B!?']2%%'#@'a7N4*44Y5444*44b
U&%"A0D&'Q12>P">/&
744 94 64 84
777N*85778
!"#$#%&'"()*$+*,-&-*%(,#'.)/(*%($',,(0001234567 7776*85K;7
$KLM( 0005234567
