Table 1.

¹H-NMR data for the natural pheromone preparation (compounds I and II) and for synthetic 5 and 6 (see Fig. 3)

Group	Position	δH, ppm			δH, ppm
		in CD2Cl2		in D2O	in CD2Cl2		in c-Hex.	J couplings, Hze
		Nat. IIa	[5]b	[5]c	Nat. Ia	[6](mix.)b	[6]d	Nat. II		Nat. I
CH3	1	0.9025	0.9024	0.9184	0.8718	0.8716	0.8676	3J(1,2)	6.58	6.52
	1′	0.8949	0.8947	0.9135					6.69
CH	2	2.1125	2.1132	2.094	1.8225	1.8225	1.869f	3J(2,3)	7.13(3a); 6.63(3b)	7.06
CH2	3a	2.3345	2.3352	2.52	1.9012	1.9000	1.901f	1J(3a,b)	−16.54
	3b	2.2888	2.2889	2.50				5J(3,6)		1.11
								5J(3,10)		0.48
CH	5	2.4523	2.4531	2.704				3J(5,6)	7.08; 5.72
CH2	6a	1.67g	1.67h	1.67i	1.9060	1.9052	1.882f	3J(6,7)	n.d.g	6.74
	6b	1.36g	1.36h	1.44i				4J(6,10)		0.98
CH2	7a	1.38g	1.38h	1.48i	1.5582	1.5577	1.5237	3J(6,7)	n.d.g
	7b	1.33g	1.33h	1.40i
−OH	8	1.51j	2.9; 4.15k
CH3	9	1.1735	1.1736	1.209	1.1590	1.1563	1.1325	4J(9,9′)	0.21
	9′	1.1710	1.1700
CH3	10	1.0486	1.0488	1.0856	1.5807	1.5802	1.5647	3J(5,10)	7.00
rms dev.l			0.00046	0.114		0.0012	0.026

^aNatural pheromone preparation (mixture of I and II), shifts relative to CHDCl₂ = 5.32 ppm (30°C). 

^bMixture of 5 and 6 derived from synthetic 5 (30°C). 

^cNearly pure 5 in D₂O, HDO = 4.75 ppm (30°C). 

^dPure 6 in cyclohexane-d₁₂ at 15°C (solvent = 1.38 ppm). 

^e4J(1,3) for I and II, ⁴J(7,9) for I detected by COSY. 

^fDetermined from the coloc 2D CH correlation experiment. 

^gComplex second-order spin systems; δ_H from COSY spectrum; n.d., not determined. 

^hMultiplets superimposable with those of II. 

ⁱEstimated shifts assigned by analogy to II. 

^jResidual water. 

^kFor pure synthetic 5 as neat liquid. 

^lrms deviation of all shifts (except 8-OH) relative to natural compound.