Table 2.

¹³C-NMR data for the natural pheromone preparation and the synthetic compounds 5 and 6

Position	δc, ppma		Predictionsb		δc, ppma			Predictionsb
	in CD2Cl2, 10°C		ketone [5]		in CD2Cl2		in c-Hex.	Dihydropyran [6]		enol [5b]
	Nat. II	[5](mix).	S. Tool	S. Edit	Nat. I	[6](mix.)	[6]	S. Tool	S. Edit	S. Tool	S. Edit
1	22.643	22.796	21.8	22.0  (4)	22.382	22.554	22.880	22.7	23.0  (3)	22.7	23.0  (3)
1′	22.571	22.720
2	24.350	24.426	22.4	25.0  (3)	27.099	27.155	27.478	22.9	27.0  (2)	22.6	27.0  (2)
3	50.377	50.511	47.7	43.0  (2)	39.655	39.775	40.299	41.6	26.0  (2)	43.5	26.0  (2)
4	214.404	214.795	211.3	213.0  (2)	145.456	145.585	146.526	149.8	149.0 (2)	149.4	162  (1)
5	46.902	47.069	47.4	44.0  (2)	100.677	100.599	99.719	100.8	137  (1)	105.9	137  (1)
6	27.531	27.682	21.8	27.0  (2)	25.280	25.394	25.942	27.2	31.0  (2)	21.0	31.0  (2)
7	41.380	41.473	43.0	34.0  (2)	33.612	33.733	34.320	43.5	34.0  (2)	43.8	34.0  (2)
8	70.677	70.544	68.7	71.0  (3)	72.118	72.157	72.041	69.4	76.0  (2)	69.1	71.0  (3)
9	29.261	29.413	30.1	29.0  (4)	26.501	26.651	26.970	28.0	28.0  (3)	30.2	29.0  (4)
9′	29.210	29.227
10	16.480	16.657	13.7	15.0  (3)	17.945	18.086	18.244	12.9	20.0  (2)	12.9	20.0  (2)
rms dev.c		0.172	2.43	3.20		0.118	0.642	4.21		4.98

^aComparing the natural isolated mixture I + II (ca. 5 mM) with a synthetic mixture derived from 5 (ca. 1 M) in CD₂Cl₂ at 10°C (CD₂Cl₂ = 53.80 ppm), and with pure 6 (ca. 1 M) in cyclohexane-d₁₂ at 15°C (solvent = 26.40 ppm); assignments for natural material obtained by CH correlation, including discrimination of 1,1′ and 9,9′ for the ketone. 

^bShift predictions made with spectool and with win-specedit based on (n) spheres of HOSE code; bold highlights data where spectool predictions favor dihydropyran 6. 

^crms deviation of all shifts relative to those for the natural material.