Table 1.

NMR data of hapalindole X (1) in CDCl₃

Position	δC, mult.a	δH	mult. (J in Hz)b	COSYb	HMBCb	NOESYb
1		8.07	br s	2		2
2	118.8, CH	7.67	t (1.7)	1, 10c	3, 8, 9	1, 10, 11
3	113.4, C
4	140.7, C
5	113.2, CH	7.02	d (6.8)	6	7, 9, 16	17, 18
6	123.3, CH	7.18	t (6.8)	5, 7	4, 8
7	108.54, CH	7.18	d (6.8)		5, 9
8	133.7, C
9	125.2, C
10	42.7, CH	3.08	t (11.1)	11, 15	2, 3, 11, 15	11, 14ax, 15, 18
11	63.0, CH	4.24	d (11.1)	10, 19a, 19b	10, 12	10, 13, 15
12	144.7, C
13	45.9, CH	2.64	br t	14eq, 14ax, 20		11, 14eq, 15, 20
14eq	33.1, CH2	2.11	dt (12.6, 3.0)	13, 14ax, 15	10, 12	13, 14ax, 15
14ax		1.38	ddd (12.6)	13, 14eq, 15	10, 12, 13, 15, 20	10, 14eq, 18
15	48.7, CH	1.77	ddd (12.6, 11.1, 3.0)	10, 14eq, 14ax		11, 13, 14eq
16	37.9, C
17	25.08, CH3	1.48	s	18	4, 15, 16, 18	5
18	25.05, CH3	1.08	s	17	4, 15, 16, 17	5, 10
19a	108.53, CH2	5.45	t (1.7)	11	11, 12, 13	11, 19b
19b		5.06	t (1.7)	11	11, 13	19a, 20
20	139.1, CH	5.94	ddd (17.6, 10.4, 7.8)	13, 21E, 21Z	13, 14	14ax, 21E, 21Z
21E	116.3, CH2	5.19	dd (10.4, 1.7)	20	13
21Z		5.14	dt (17.6, 1.7)	20	13, 20	13, 20
22	159.5, C

^aRecorded at 225 MHz.

^bRecorded at 600 MHz.

^cA four-bond correlation resulting from “W” configuration.