Table 1.

NMR Spectroscopic Data for Metacridamides A (1) and B (2)

metacridamide A (1)a				metacridamide B (2)b
position	δC, mult.c	δH (J in Hz)d	HMBCe	δCf	δH (J in Hz)d	HMBCe
2	170.9, qC			173.1
3	53.0, CH	4.94, m	2, 5, 25	54.4	4.85 br, s
4		5.91, d (8.6)	2g, 3, 5, 25		8.21, d (9.1)	3, 5
5	168.7, qC			172.6
6	132.7, qC			132.5
7	133.7, CH	6.03, dd (9.5, 1.4)	5, 8g, 9, 30, 31	136.9	6.15, d (9.5)	5, 30
8	35.5, CH	2.84, m	6, 7, 9g, 31	36.8	2.81h, m	6, 7, 31
9	78.3, CH	3.95, s	7, 8, 10, 11, 31, 32, 33g,i	79.3	3.94, s	7, 8, 10, 11, 31, 32, 33g,i
10	137.1, qC			136.3
11	124.3, CH	5.02, m	9, 10g, 12g, 13g, 32, 33	127.4	5.26, d (10.5)	9, 32, 33
12	36.6, CH	2.83, m	9g,i, 10, 11, 13, 33	40.7	2.73, ddd (10.5, 7.0, 3.6)	10, 11, 13, 33
13	81.4, CH	4.92, m	11, 12, 14, 15, 33, 34, Ac C=O	81.0	3.84, d (10.2)	11, 12, 14, 15, 33, 34
14	130.9, qC			136.0
15	131.0, CH	5.11, dd (10.0)	13, 16, 17, 34, 35g	130.3	5.12, d (10.2)	13, 16, 17, 34, 35
16	33.5, CH	2.71, m	14, 15, 35	35.5	2.81h, m	14, 15, 35
17	82.7, CH	4.61, dd (8.8, 2.3)	2, 15, 16, 18, 19, 23, 35	83.7	4.68, dd (8.0, 1, 8)	2, 15, 16g, 18g, 19, 23, 35
18	33.7, CH	1.61, m	19, 20, 23	35.2	1.70, m	19g
19	40.2, CH2	1.10, ddd (13.3, 9.5, 3.8)	17, 18, 20, 21, 23, 24	42.3	1.29, m	18, 20, 21, 23, 24
		0.84, m	17, 18, 20, 21, 23, 24		0.91, m	18, 20, 21, 23, 24
20	31.2, CH	1.38, m		33.0	1.43, m
21	27.6, CH2	1.28, m	19, 20, 22g, 24	29.4	1.39, m	19g, 20, 22g, 24
		0.84, m	19, 20, 22, 24		0.96, m	19g, 20, 22, 24
22	10.8, CH3	0.74, t (7.4)	20, 21	11.7	0.85, t (7.4)	20, 21
23	16.0, CH3	0.75, d (6.7)	17, 18, 19	16.3	0.77, d (6.7)	17, 18, 19
24	20.5, CH3	0.81, d (6.6)	19, 20, 21	20.8	0.88	19, 20, 21
25	36.5, CH2	3.27, dd (14.0, 6.1)	2, 3, 26, 27	37.2	3.33, dd (14.1, 5.4)	2, 3, 26, 27
		3.20, dd (14.0, 5.8)	2, 3, 26, 27		2.95, dd (14.1, 10.2)	2, 3, 26, 27
26	137.0, qC			139.5
27, 27’	129.8, CH	7.20, m	25, 29	130.4	7.233, m	25, 29
28, 28’	128.6, CH	7.27, m	26, 27g	129.4	7.235, m	26
29	127.0, CH	7.21, m	27, 28g	127.6	7.17, m	27, 28g
30	13.1, CH3	1.83, d (1.4)	5, 6, 7, 8g,j, 9g,i, 31g,i	13.6	1.65, d (1.4)	5, 6, 7, 31g,i
31	19.4, CH3	1.19, d (7.0)	7, 8, 9	19.3	1.18, d (7.0)	6g,j, 7, 8, 9
32	15.0, CH3	1.61, m	8g,j, 9, 10, 11, 12g,j	15.2	1.60, d (0.6)	9, 10, 11
33	16.1, CH3	0.92, d (7.0)	11, 12, 13, 34g,i	16.1	0.93, d (7.0)	11, 12, 13, 34g,i
34	13.6, CH3	1.63, d (1.3)	12g,j, 13, 14, 15, 16g,j, 35i	13.7	1.67, d (1.3)	12g,j, 13, 14, 15, 35g,i
35	18.2, CH3	0.67, d (6.9)	15, 16, 17	19.8	1.02, d (6.9)	15, 16, 17
Ac C=O	169.8, qC
Ac CH3	21.4, CH3	2.04, s	Ac C=O, 13g,i

^aCDCl₃.

^bCD₃OD (assignments and correlations for H4 obtained in CD₃OH).

^c150MHz.

^d600 MHz.

^eHMBC correlations, optimized for 8 MHz, are from proton(s) stated to the indicated carbon.

^f125 MHz.

^gWeak crosspeak.

^hOverlapping signals.

ⁱ5-bond correlation (Figures S16, S32).

^j4-bond correlation.