. Author manuscript; available in PMC: 2014 Mar 18.

Published in final edited form as: J Nat Prod. 2011 Feb 22;74(3):430–440. doi: 10.1021/np1008637

Table 5.

Specific rotations and Configurational Assignment of bis-Piperidine Alkaloids.^a

cmpd.	[α]_D	conc. g/100 mL, solvent		linker chain C_n		absolute confign.^a

				top	bottom
1^b	+4.4	c 2.0,	CH₃OH	C₁₀	C₁₀	2R,3S,7S,9S
2^b	+2.7	c 2.4,	CH₃OH	C₁₀	C₁₀	2R,3S,7S,9S
3^b	−18.5	c 0.67,	CHCl₃	C₁₀	C₁₀	2S,3S,7S,9S,23S
4^c	−7.3	c, 0.73,	CH₂Cl₂	C₈	C₁₂	2R,3S,9R* ^h
5^d	−143.5	c, 0.65,	?	C₁₀	C₈	2R,3S,7S* _h
6^e	−3.4	c 1.21,	CH₂Cl₂	C₁₀	C₁₂	2R,3R,7R,9R
7^e	+3.4	c 0.55,	CH₂Cl₂	C₁₀	C₁₂	2R,3R,7R,9R
8^f	−3	c 0.015,	MeOH	C₁₀	C₁₂	2R,3S,7S,9S ^b
9^f	+14	c 0.02,	MeOH	C₁₀	C₁₂	2R,3S,7S,9S ^b
26^g	−20.9	c 0.205,	CHCl₃	C₁₀	C₁₂	2S,3S,7S,9S
31^g	+19.4	c 0.515,	CHCl₃	C₁₀	C₁₂	2S,3S,7S,9S
32ⁱ	−10	c 1.0,	CHCl₃	C₁₀	C₁₀	2R,3R,7R,9R^h

Core locants follow the numbering used for 1–3. Unless indicated by *, depicted CIP assignments are absolute. Configuration of the N atoms not given.

this work.

ref. ⁴.

X-ray, ref. 5.

X-ray, ref. 6a.

ref. ⁷.

X-ray, ref. 15.

relative configuration only.

ref. ²⁰.