oh h ch h nmr (400 mhz, cdcls14 13c nmr (100 mhz, cdcl 3) ch3 h h3c h oh oh 4 200 150 100 50 0 [ppm]...
TRANSCRIPT
![Page 1: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/1.jpg)
S13
1H NMR (400 MHz, CDCl3) CH3
H
H3C
H
OH
OH
4
[ppm] 5 4 3 2 1
[rel]
0
5
10
1.00
00
1.04
73
1.02
49
1.14
73
2.24
36
3.10
573.
1200
2.76
263.
4481
3.44
09
4.51
02
jasondiol 1 1 C:\Users\hovseps\nmr-data
[ppm] 8 6 4 2
[rel
] 0
5
1
0 1
5
jasondiol 1 1 C:\Users\hovseps\nmr-data
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2016
![Page 2: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/2.jpg)
S14
13C NMR (100 MHz, CDCl3) CH3
H
H3C
H
OH
OH
4
[ppm] 200 150 100 50 0
[rel
] 0
5
1
0 1
5 2
0
"Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data
![Page 3: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/3.jpg)
S15
1H NMR (400 MHz, CDCl3) CH3
H
CH3
H3C
H
O
5
[ppm] 8 6 4 2
[rel
] 0
2
4
6
8
1
0 1
2 1
4
transketonepossibly 1 1 C:\Users\hovseps\nmr-data
[ppm] 2.5 2.0 1.5 1.0 0.5 [r
el]
0
5
10
1.00
00
2.17
25
1.03
03
1.12
60
2.01
39
1.23
86
3.18
31
2.13
19
3.00
42
3.11
81
2.97
29
transketonepossibly 1 1 C:\Users\hovseps\nmr-data
![Page 4: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/4.jpg)
S16
13C NMR (100 MHz, CDCl3)
CH3
H
CH3
H3C
H
O
5
[ppm] 200 150 100 50 0
[rel
] 0
2
4
6
transexpandedcarbon 1 1 C:\Users\hovseps\nmr-data
![Page 5: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/5.jpg)
S17
1H NMR (400 MHz, CDCl3)
[ppm] 8 6 4 2
[rel
] 0
2
4
6
8
1
0 1
2 1
4
cisketonepure 1 1 C:\Users\hovseps\nmr-data
[ppm] 2.5 2.0 1.5 1.0 0.5 [r
el]
0
2
4
6
8
10
12
14
3.00
00
3.02
113.
2350
1.07
12
3.11
83
1.82
61
2.19
56
3.04
51
1.08
18
1.45
09
cisketonepure 1 1 C:\Users\hovseps\nmr-data
6
CH3
H
CH3
H3C
H
O
![Page 6: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/6.jpg)
S18
13C NMR (100 MHz, CDCl3)
[ppm] 200 150 100 50 0
[rel
] 0
5
1
0 1
5 2
0 2
5
cisketonepureJune 2 1 C:\Users\hovseps\nmr-data
6
CH3
H
CH3
H3C
H
O
![Page 7: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/7.jpg)
S19
1H NMR (400 MHz, CDCl3) CH3
H
CH3
H3C
O
7
[ppm] 8 6 4 2 0
[rel
] 0
2
4
6
8
1
0 1
2 1
4
cisexpandedketonenew 1 1 C:\Users\hovseps\nmr-data
[ppm] 3.0 2.5 2.0 1.5 1.0 0.5 - 0.0
[rel
] 0
5
1
0
1.00
00
2.18
30
1.10
51
1.36
60
2.29
79
1.62
02
2.07
44
3.10
09
3.36
613.
2501
4.43
93
1.55
34
cisexpandedketonenew 1 1 C:\Users\hovseps\nmr-data
![Page 8: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/8.jpg)
S20
13C NMR (100 MHz, CDCl3)
CH3
H
CH3
H3C
O
7
[ppm] 200 150 100 50 0
[rel
] 0
5
1
0 1
5 2
0
cisexpandedketonenew 2 1 C:\Users\hovseps\nmr-data
![Page 9: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/9.jpg)
S21
1H NMR (400 MHz, CDCl3) 9CH3
H
CH3
H3C
O
[ppm] 8 6 4 2 0
[rel
] 0
2
4
6
8
1
0 1
2 1
4
enone 1 1 C:\Users\hovseps\nmr-data
[ppm] 8 6 4 2
[rel
] 0
5
1
0
1.00
00
1.00
21
1.00
82
2.29
83
3.16
14
2.23
08
1.24
97
3.00
01
2.19
96
6.29
08
enone 1 1 C:\Users\hovseps\nmr-data
![Page 10: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/10.jpg)
S22
13C NMR (100 MHz, CDCl3)
9CH3
H
CH3
H3C
O
[ppm] 200 150 100 50 0
[rel
] 0
1
0 2
0 3
0 4
0 5
0
enone 2 1 C:\Users\hovseps\nmr-data
![Page 11: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/11.jpg)
S23
1H NMR (400 MHz, CDCl3), as a 10:1 mixture of stereoisomers. CH3
H
CH3
H3C
OMs
O
10
[ppm] 8 6 4 2 0
[rel
] 2
4
6
8
1
0 1
2 1
4
MesylatedEpoxyy 1 1 C:\Users\hovseps\nmr-data
[ppm] 4 3 2 1
[rel
] 0
5
1
0 1
5
1.00
00
3.17
00
1.18
58
4.48
25
1.32
70
3.71
76
3.03
17
3.31
37
7.00
68
2.58
67
MesylatedEpoxyy 1 1 C:\Users\hovseps\nmr-data
![Page 12: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/12.jpg)
S24
13C NMR (100 MHz, CDCl3), as a 10:1 mixture of stereoisomers.
CH3
H
CH3
H3C
OMs
O
10
[ppm] 200 150 100 50 0
[rel
]- 0
1
2
3
4
MesylatedEpoxyy 2 1 C:\Users\hovseps\nmr-data
![Page 13: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/13.jpg)
S25
NOESY Ha Hb CH3d Hf CH3e
F2 (ppm)
1.01.52.02.53.03.54.04.55.05.5
F1(ppm)
1
2
3
4
5
6
F2 (ppm)
1.01.52.02.53.03.54.04.55.05.5
F1(ppm)
1
2
3
4
5
6
F2 (ppm)
1.01.52.02.53.03.54.04.55.05.5
F1(ppm)
1
2
3
4
5
6
Plotname: --Not assigned--
H3C
Hf
CH3
H3C
OO
Ha
SOO
H3C
Hb
Hb
10d
e
![Page 14: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/14.jpg)
S26
1H NMR (400 MHz, acetone-d6) CH3
H
CH3
H3C
O
Hortonone C
[ppm] 8 6 4 2 0
[rel
] 0
2
4
6
8
1
0 1
2 1
4
HortononeC 1 1 C:\Users\hovseps\nmr-data
[ppm] 6 5 4 3 2 1
[rel
] 0
5
1
0 1
5
1.00
00
1.00
11
1.11
54
2.32
37
1.23
29
1.02
772.
6741
1.89
80
3.21
693.
2757
3.27
40
HortononeC 1 1 C:\Users\hovseps\nmr-data
![Page 15: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/15.jpg)
S27
13C NMR (100 MHz, acetone-d6)
CH3
H
CH3
H3C
O
Hortonone C
[ppm] 200 150 100 50 0
[rel
]- 0
.0
0.5
1
.0
1.5
2
.0
2.5
HortononeC 2 1 C:\Users\hovseps\nmr-data
![Page 16: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/16.jpg)
S28
1H NMR (400 MHz, CDCl3)
CH3
H
CH3
H3C
H3C
O
Hortonone A
[ppm] 6 4 2
[rel
] 0
2
4
6
8
1
0 1
2
"Hortonone A" 3 1 C:\Users\hovseps\nmr-data
[ppm] 8 6 4 2 [r
el]
- 2
0
2
4
6
8
10
1.00
00
1.05
10
1.13
48
1.15
18
4.11
693.
3378
4.01
87
6.96
593.
3587
1.56
51
1.35
62
"Hortonone A" 3 1 C:\Users\hovseps\nmr-data
![Page 17: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/17.jpg)
S29
13C NMR (100 MHz, CDCl3)
CH3
H
CH3
H3C
H3C
O
Hortonone A
[ppm] 200 150 100 50
[rel
] 0
5
1
0 1
5
"Hortonone A" 4 1 C:\Users\hovseps\nmr-data
![Page 18: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/18.jpg)
S30
1H NMR (400 MHz, CDCl3) CH3
H
CH3
H3C
O
HO
Hortonone B
[ppm] 8 6 4 2
[rel
] 0
5
1
0 1
5 2
0
1.00
00
1.92
32
1.04
79
1.18
530.
8928
1.25
16
8.14
843.
1348
2.13
582.
8388
1.20
863.
1890
3.38
27
3.93
13
"hortonone b last" 1 1 C:\Users\hovseps\nmr-data
[ppm] 6 4 2
[rel
] 0
1
0 2
0 3
0 4
0 5
0
"hortonone b last" 1 1 C:\Users\hovseps\nmr-data
![Page 19: OH H CH H NMR (400 MHz, CDClS14 13C NMR (100 MHz, CDCl 3) CH3 H H3C H OH OH 4 200 150 100 50 0 [ppm] [rel] 0 5 10 15 20 "Lythgoe Diol" 3 1 C:\Users\hovseps\nmr-data](https://reader033.vdocuments.site/reader033/viewer/2022041816/5e5b3773baf0484464418a49/html5/thumbnails/19.jpg)
S31
13C NMR (100 MHz, CDCl3
CH3
H
CH3
H3C
O
HO
Hortonone B
[ppm] 200 150 100 50 0
[rel
]- 0
.0
0.5
1
.0
1.5
2
.0
2.5
"hortonone b last" 2 1 C:\Users\hovseps\nmr-data