supplementary information1 supplementary information functionalization of diazotetronic acid and...
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Supplementary Information
Functionalization of Diazotetronic Acid and Application in a Stereoselective Modular
Synthesis of Pulvinone, Aspulvinones A-E, G, Q and their Analogues
Amarender Manchoju, Ritesh A. Annadate, Lise Desquien and Sunil V. Pansare*
Department of Chemistry, Memorial University of Newfoundland
St. John’s, Newfoundland, Canada A1B 3X7
1H and 13C Spectra……………………………………………………………………………...2-40
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2018
2
11a
1H NMR (300 MHz, CDCl3)
11a
13C NMR (75 MHz, CDCl3)
3
11b
1H NMR (300 MHz, CDCl3)
11b
13C NMR (75 MHz, CDCl3)
4
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
AM-11-139
11c 1H NMR (300 MHz, CDCl3)
11c 13C NMR (75 MHz, CDCl3)
5
11d
1H NMR (300 MHz, CDCl3)
11d
13C NMR (75 MHz, CDCl3)
6
7
11f
1H NMR (300 MHz, CDCl3)
11f
13C NMR (75 MHz, CDCl3)
8
6.04
8.83
3.06
1.00
1.07
1.19
1.04
-0.0
00.
18
1.00
3.86
6.65
6.86
6.89
7.22
7.23
7.25
7.26
7.26
7.33
7.34
-4.4
2
0.14
18.6
5
25.7
8
55.6
7
76.7
477
.16
77.5
8
112.
6311
4.50
121.
4112
4.91
126.
10
140.
66
148.
0415
1.36
160.
51
174.
74
9
0102030405060708090100110120130140150160170180f1 (ppm)
AM-11-75
11h
1H NMR (300 MHz, CDCl3)
11h
13C NMR (75 MHz, CDCl3)
10
11i
1H NMR (300 MHz, CDCl3)
11i
13C NMR (75 MHz, CDCl3)
11
O O
O N2
11j
1H NMR (300 MHz, CDCl3)
11j
13C NMR (75 MHz, CDCl3)
12
O O
O N2
F3C 11k
1H NMR (300 MHz, CDCl3)
11k
13C NMR (75 MHz, CDCl3)
13
11l
1H NMR (300 MHz, CDCl3)
11l
13C NMR (75 MHz, CDCl3)
14
O
O N2
O
1H NMR (500 MHz, DMSO-d6)
O2N11m
15
11n
1H NMR (300 MHz, CDCl3)
11n
13C NMR (75 MHz, CDCl3)
16
11o
1H NMR (300 MHz, CDCl3)
11o
13C NMR (75 MHz, CDCl3)
17
-0.0
1
1.23
5.91
7.26
0.13
29.7
032
.95
76.7
477
.16
77.5
8
124.
82
142.
27
160.
34
175.
18
18
3.19
2.62
0.81
1.00
0.99
0.86
1.92
1.76
1.25
0.91
1.74
0.01
1.57
2.35
2.36
2.67
4.84
4.84
4.98
4.99
5.13
5.14
5.18
5.30
7.17
7.19
7.19
7.21
7.25
7.26
7.26
7.32
7.34
21.5
721
.61
72.7
373
.92
77.1
877
.44
77.6
9
86.9
086
.98
126.
9212
7.21
129.
7412
9.86
133.
7713
5.81
139.
1913
9.22
163.
2916
3.79
186.
2318
7.10
19
13a
1H NMR (300 MHz, CDCl3/DMSO-d6)
13a
13C NMR (75 MHz, CDCl3/DMSO-d6)
20
13b 1H NMR (300 MHz, CDCl3)
13b
13C NMR (75 MHz, CDCl3)
21
14a
1H NMR (300 MHz, CDCl3/CD3OD, 97:3)
14a
13C NMR (75 MHz, DMSO-d6)
22
14b
1H NMR (300 MHz, CDCl3)
14b
13C NMR (75 MHz, CDCl3)
23
15
15
13C NMR (75 MHz, CDCl3)
24
-100102030405060708090100110120130140150160170180190200210
O
HO
O
TBSOOMe
OTBS
1H NMR (300 MHz, DMSO-d6)
16
25
19
1H NMR (300 MHz, CDCl3)
19
13C NMR (75 MHz, CDCl3)
26
-3.9
5
18.0
318
.45
22.6
125
.88
26.9
928
.71
32.7
6
74.8
976
.74
77.1
677
.58
103.
09
108.
68
118.
0611
8.99
119.
9212
1.95
122.
3812
5.83
126.
8612
9.23
129.
6113
2.67
132.
8813
3.14
140.
12
154.
2715
4.77
160.
59
169.
11
27
28
-10010203040506070809010011012013014015016017018090
O
HO
O
O
TBSO
TBSO
13C NMR (75 MHz, CDCl3)
22
29
23
1H NMR (300 MHz, CDCl3/CD3OD, 95:5)
23
13C NMR (75 MHz, CDCl3/CD3OD, 95:5)
30
24
1H NMR (300 MHz, DMSO-d6)
24
13C NMR (75 MHz, DMSO-d6)
31
32
1
1H NMR (300 MHz, DMSO-d6)
1
13C NMR (75 MHz, DMSO-d6)
33
2
1H NMR (300 MHz, CD3OD)
2
13C NMR (75 MHz, CD3OD)
34
O O
HO
OH
HO
OH
3
1H NMR (300 MHz, CD3OD)
3
13C NMR (75 MHz, CD3OD)
35
4
1H NMR (300 MHz, acetone-d6)
O O
HO
OH
HOOH
4
13C NMR (75 MHz, CD3OD)
36
0102030405060708090100110120130140150160170180190
37
6
1H NMR (300 MHz, CDCl3/DMSO-d6, 95:5)
O O
HO
O
O
6
13C NMR (75 MHz, DMSO-d6)
38
7
1H NMR (300 MHz, DMSO-d6)
7
13C NMR (75 MHz, DMSO-d6)
39
40