Electronic Supplementary Information Preparation of oxocene

Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
This journal is © The Royal Society of Chemistry 2016
Electronic Supplementary Information
Preparation of oxocene terpenes. First enantiospecific
synthesis of cytotoxic arenaran A
Alejandro Torres,a Pilar Gutierrez, a Ramón Alvarez-Manzaneda,b Rachid Chahboun* a
and Enrique Alvarez-Manzaneda* a
a
Departamento de Química Orgánica, Facultad de Ciencias, Instituto de Biotecnología,
Universidad de Granada, 18071 Granada, Spain.
b
Área de Química Orgánica, Departamento de Química y Física, Universidad de Almería,
04120 Almería, Spain.
*E mail: [email protected]; [email protected]
Contents
1
H and
13
C NMR Spectra for all new compounds, 1D NOESY for
compound 1, and 1D TOCSY, COSY, HSQC, HMBC and 1D NOESY for
compound 2
O
H
1
Recorded at 400 MHz in CDCl3
O
H
1
Recorded at 100 MHz in CDCl3
O
H
1
Recorded at 400 MHz in C6D6
O
H
1
Recorded at 100 MHz in C6D6
O
O
H
2
O
O
H
2
O
4
O
4
OH
5
OH
5
O
9
O
9
OH
10
OH
10
O
11
O
11
O
12
O
12
O
H
13
O
H
13
H
15
H
15
O
O
18
O
O
18
O
O
O
19
O
O
O
19
O
23
O
23
OH
H
26
OH
H
26
O
H
27
O
H
27
O
H
28
O
H
28
O
O
H
29
O
O
H
29
Select NOE of compound 1
13
1
8
2
9
7
10
6
11
3
5
14
15
4
12
13
1
8
2
9
7
10
6
11
3
5
14
15
4
12
13
1
8
2
9
7
10
6
11
3
5
14
15
4
12
13
1
8
2
9
7
10
6
11
3
5
14
15
4
12
13
1
8
2
9
7
10
6
11
3
5
14
4
12
15
1D TOCSY
13
1
8
2
9
7
10
6
11
3
5
14
4
12
15
1D TOCSY
Stacked Proton and 1D TOCSY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
Edited HSQC
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
Edited HSQC
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
Edited HSQC
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
COSY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
COSY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
HMBC
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
HMBC
13
8
O
9
10
1
2
7
6
11
H
O
5
4
14 15
HMBC
3
12
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
1D NOESY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
1D NOESY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
1D NOESY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
1D NOESY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
1D NOESY
13
8
O
9
10
1
2
7
6
11
H
O
5
4
3
12
14 15
1D NOESY