Table XIII.

¹H NMR Data of Hemanthamine-Type Alkaloids

Alkaloid	42	43	44	45	46	47	48/49	53	54	55/56	57	58
H-1	6.44 d	6.41 d	6.71 d	6.65 d	6.58 d	6.49 d	6.65 d/6.66 d	6.36 d	6.40 d	6.33 d	6.22 br s	6.48 d
H-2	6.06 dd	6.19 dd	5.93 dd	5.99 dd	5.91 ddd	6.08 dd	6.00 dd	6.25 dd	6.21 dd	6.27 dd	6.22 br s	6.35 dd
H-3	4.46 m	4.28 ddd	4.27 ddd	4.36 m	4.31 td	3.85 m	3.88 m/3.85 m	3.82 m	3.91 m	3.85 m	3.98 m	3.86 m
H-4α	1.85 ddd	2.28 ddd	1.81 ddd	1.75 ddd	1.73 td	1.73 ddd	1.77 ddd/1.60 ddd	2.11 ddd	2.07 ddd	2.36 ddd/2.21 ddd	2.08 m	2.11 ddd
H-4β	2.58 ddd	1.85 ddd	1.95 m	2.03 ddd	1.90 dddd	2.95 ddd	2.21 br d/2.09 m	1.96 ddd	1.98 ddd	2.12 ddd/2.00 ddd	2.08 m	2.04 ddd
H-4a	3.87 m	3.47 dd	3.48 dd	3.37 m	3.43 dd	3.90 dd	3.59 dd/3.90 m	3.25 dd	3.41 m	3.56 dd/3.20 m	3.22 dd	3.38 m
H-6α	4.07 d	3.84 d	3.84 d	3.79 d	3.81 d	4.25 d	—/5.16 s	3.72 d	3.77 d	—/5.02 s	3.66 d	3.70 d
H-6β	4.71 d	4.35 d	4.39 d	4.39 d	4.41 d	4.80 d	5.86 s/—	4.25 d	4.40 d	5.69 s/—	4.28 d	4.31 d
H-7	6.53 s	6.56 s	6.66 s	6.56 s	6.53 s	6.57 s	7.03 s/6.89 s	6.41 s	6.52 s	6.94 s/6.79 s	6.47 s	6.53 s
H-10	6.87 s	6.94 s	6.97 s	6.82 s	6.87 s	6.81 s	6.80 s/6.83 s	6.74 s	6.95 s	6.70 s/6.73 s	6.79 s	6.78 s
H-11 endo	2.15 m	3.98 dd	1.95 m	1.95 m	1.8–2.0 m	2.22 ddd	2.00 m	3.96 dd	5.05 dd	3.92 m	3.92 m	3.99 ddd
H-11 exo	2.32 m	—	2.17 m	2.15 m	2.19 ddd	2.37 ddd	2.00 m	—	—	—	—	—
H-12 endo	3.17 m	3.20 dd	2.93 ddd	2.95 m	2.91 ddd	3.27 ddd	3.02 ddd/2.84 ddd	3.30 dd	3.41 m	4.20 dd/3.30 m	3.40 m	3.39 m
H-12 exo	3.87 m	3.50 dd	3.34 m	3.37 m	3.31 ddd	4.08 ddd	3.73 ddd/3.39 m	3.19 dd	3.41 m	2.96 dd/3.20 m	3.40 m	3.26 dd
OCH2O	5.95 s	5.89 s	—	—	—	—	—	5.81 (2d)	5.95 s	5.83 (2d)/5.86 (2d)	5.86 s	—
OMe	—	—	3.81 s	3.89 s	3.82 s	3.86 s	3.88 s	—	—	—	—	3.86 s
OMe	—	—	3.77 s	—	—	3.82 s	3.88 s	—	—	—	—	—
OMe	—	—	—	—	—	3.34 s	3.37 s/3.31 s	3.36 s	3.41 s	3.32 s/3.28 s	3.40 s	3.35 s
OAc	—	—	—	—	—	—	—	—	2.03 s	—	—	—
Solvent	d	c	c	d	d	d	d	d	d	d	d	d
MHz	360	270	300	360	200	200	200	360	500	360	300	360
Reference	(331)	(376)	(336)	(331)	(111)	(137)	(135)	(331)	(74)	(331)	(298)	(161)
Solvent a: DMSO-d6, b: CDC13-CDC3OD, c: CD3OD, d: CDCl3

Alkaloid	59	61
H-1ax	1.77 ddd	6.38 d (1H)
H-1eq	2.39 dt
H-2ax	1.61 dddd	6.08 dd (1H)
H-2eq	2.06 m
H-3	4.67 tt (β)	3.89 ddd (α)
H-4ax	1.44 ddd	2.43 ddd
H-4eq	2.23 m	2.06 ddd
H-4a	3.18 dd	3.29 dd
H-6α	3.91 d	4.04 d
H-6β	4.50 d	4.45 d
H-7	6.48 s	6.57 s
H-10	6.74 s	6.81 s
H-11 exo	2.30 ddd	3.93 dd
H-11 endo	1.83 ddd	—
H-12 exo	3.60 m	4.82 d
H-12 endo	2.94 m	4.51 d
OMe	3.82 s	3.36 s
OCH2O	—	5.91 s
CHA	—	4.27 dd
CHB	—	3.58 dd
OAc	2.02 s	2.00 s
Solvent	d	d
MHz	500	500
Reference	(140)	(74)

Solvent a: DMSO-d₆, b: CDCl₃-CD₃OD, c: CD₃OD, d: CDCl₃.