Punctaporonins N–S, New Caryophyllene Sesquiterpenoids from Cytospora sp.

Table 3

NMR spectroscopic data for punctaporonins R (5) and S (6) in acetone-d₆.

Position	5		6
	, mult.	(J in Hz)	, mult.	(J in Hz)
1	51.2, qC		53.6, qC
2	43.8, CH	2.09, t (7.3)	39.2, CH	2.01, ddd (12.4, 7.8, 1.4)
3a	35.8, CH2	2.02, dd (7.3, 5.5)	37.8, CH2	2.37, dd (12.4, 9.2)
3b		1.54, t (5.5)		1.73, dd (9.2, 7.8)
4	42.1, qC		42.2, qC
5	80.2, qC		82.6, qC
6	69.3, CH	3.47, dd (11.3, 7.3)	69.0, CH	3.66, dd (10.2, 5.5)
7a	42.9, CH2	1.71, d (11.3)	42.4, CH2	1.94, dd (12.2, 5.5)
7b				1.86, dd (12.2, 10.2)
8	53.6, qC		48.8, qC
9	149.2, CH	5.85, d (5.8)	150.0, CH	6.01, d (5.7)
10	126.8, CH	5.82, dd (5.8, 2.2)	126.8, CH	5.70, dd (5.7, 2.7)
11	90.9, CH	3.62, d (2.2)	81.3, CH	5.28, d (2.7)
12a	57.3, CH2	3.65, d (11.4)	63.6, CH2	4.88 d (10.2)
12b		4.06, dd (11.4, 7.0)		4.06, dd (10.2, 1.4)
13	23.3, CH3	1.10, s	22.9, CH3	1.14, s
14	24.2, CH3	1.08, s	23.6, CH3	1.10, s
15	27.3, CH3	1.18, s	27.9, CH3	1.11, s
16	60.7, CH3	3.19, s
OH-5		5.29, br s
OH-6		5.18, d (7.3)		3.69, (5.5)
OH-12		3.09, d (7.0)
Ac-11			20.8, CH3	1.93, s
			170.1, qC
Ac-12			21.0, CH3	1.95, s
			170.9, qC

at 150 MHz. at 500 MHz. at 100 MHz.