PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 1.06 (3H, t, J = 7.2, CH -3′), 1.23-2.15 (12H, CH -2′, CH -2′′,
3
3
2
2
CH -3′′, CH -4′′, CH -5′′, CH -6′′), 2.34 (3H, s, CH -10), 2.74 (2H, t, J = 7.6, CH -1′), 2.76 (2H, s, CH -7), 6.17 (1H, s,
2
2
2
2
3
2
2
H-3), 8.05 (1H, s, H-5).
13
C NMR spectrum (100 MHz, DMSO-d , δ, ppm): 191.61 (C-6), 159.98 (C-2), 159.73 (C-10a), 157.32 (C-4),
6
157.10 (C-9a), 121.03 (C-4a), 117.79 (C-5), 114.56 (C-5a), 113.68 (C-3), 111.98 (C-10), 81.91 (C-8), 48.10 (C-7), 34.76
(C-2′′, C-6′′), 33.35 (C-1′), 25.07 (C-4′′), 21.69 (C-3′′, C-5′′), 21.59 (C-2′), 13.93 (C-3′), 8.25 (CH -10).
3
Spiro[(4-butyl-7,8-dihydropyrano[3,2-g]chromen-2,6-dione)-8,1′-cyclohexane] (12). Yield 82%, mp 200-201°C,
C H O .
21 24
4
PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 0.98 (3H, t, J = 7.2, CH -4′), 1.25-2.11 (14H, CH -2′, CH -3′,
3
3
2
2
CH -2′′, CH -3′′, CH -4′′, CH -5′′, CH -6′′), 2.36 (3H, s, CH -10), 2.74 (2H, s, CH -7), 2.76 (2H, t, J = 7.6, CH -1′), 6.17
2
2
2
2
2
3
2
2
(1H, s, H-3), 8.06 (1H, s, H-5).
13
C NMR spectrum (100 MHz, DMSO-d , δ, ppm): 191.59 (C-6), 159.98 (C-2), 159.73 (C-10a), 157.61 (C-4),
6
157.10 (C-9a), 121.02 (C-4a), 117.80 (C-5), 114.57 (C-5a), 113.66 (C-3), 111.91 (C-10), 81.91 (C-8), 48.10 (C-7), 34.77
(C-2′′, C-6′′), 31.10 (C-1′), 30.56 (C-2′), 25.07 (C-4′′), 22.29 (C-3′), 21.69 (C-3′′, C-5′′), 13.91 (C-4′), 8.25 (CH -10).
3
Spiro[(4-propyl-7,8-dihydropyrano[3,2-g]chromen-2,6-dione)-8,1′-(4-t-butylcyclohexane)] (13). Yield 81%,
mp 231-232°C, C H O .
24 30
4
PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 0.90 [9H, s, (CH ) -4′′], 1.06 (3H, t, J = 7.2, CH -3′), 1.37-2.20
3
3 3
3
(11H, CH -2′, CH -2′′, CH -3′′, H-4′′, CH -5′′, CH -6′′), 2.36 (3H, s, CH -10), 2.72 (2H, s, CH -7), 2.74 (2H, t, J = 7.6,
2
2
2
2
2
3
2
CH -1′), 6.17 (1H, s, H-3), 8.06 (1H, s, H-5).
2
13
C NMR spectrum (100 MHz, DMSO-d , δ, ppm): 191.67 (C-6), 159.95 (C-2), 159.64 (C-10a), 157.30 (C-4),
6
157.10 (C-9a), 121.10 (C-4a), 117.89 (C-5), 114.51 (C-5a), 113.73 (C-3), 111.99 (C-10), 81.26 (C-8), 48.56 (C-7), 46.69
(C-4′′), 34.81 (C-2′′, C-6′′), 33.35 (C-1′), 32.59 [C-(CH ) ], 27.77 [(CH ) ], 22.20 (C-3′′, C-5′′), 21.58 (C-2′), 13.92 (C-3′),
3 3
3 3
8.11 (CH -10).
3
Spiro[(4-butyl-7,8-dihydropyrano[3,2-g]chromen-2,6-dione)-8,1′-(4-t-butylcyclohexane)] (14). Yield 73%,
mp 250-251°C, C H O .
25 32
4
PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 0.90 [9H, s, (CH ) -4′′], 0.98 (3H, t, J = 7.2, CH -4′), 1.36-2.20
3
3 3
3
(13H, CH -2′, CH -3′, CH -2′′, CH -3′′, H-4′′, CH -5′′, CH -6′′), 2.36 (3H, s, CH -10), 2.71 (2H, s, CH -7), 2.77 (2H, t,
2
2
2
2
2
2
3
2
J = 7.6, CH -1′), 6.17 (1H, s, H-3), 8.06 (1H, s, H-5).
2
13
C NMR spectrum (100 MHz, DMSO-d , δ, ppm): 191.61 (C-6), 159.98 (C-2), 159.68 (C-10a), 157.60 (C-4),
6
157.10 (C-9a), 121.11 (C-4a), 117.85 (C-5), 114.56 (C-5a), 113.73 (C-3), 111.93 (C-10), 81.29 (C-8), 48.59 (C-7), 46.70
(C-4′′), 34.82 (C-2′′, C-6′′), 32.59 [C-(CH ) ], 31.10 (C-1′), 30.56 (C-2′), 27.79 [(CH ) ], 22.29 (C-3′), 22.21 (C-3′′, C-5′′),
3 3
3 3
13.92 (C-4′), 8.21 (CH -10).
3
Spiro[(4-propyl-7,8-dihydropyrano[3,2-g]chromen-2,6-dione)-8,1′-(3-methylcyclohexane)] (15). Yield 59%,
mp 173-174°C, C H O .
22 26
4
PMR spectrum (300 MHz, DMSO-d , δ, ppm, J/Hz): 0.86 (3H, d, J = 7.2, CH -3′′), 0.99 (3H, t, J = 7.2, CH -3′),
6
3
3
1.05-2.00 (11H, CH -2′, CH -2′′, CH -3′′, H-3′′, CH -5′′, CH -6′′), 2.20 and 2.24 (3H, 2s, CH -10), 2.77 (2H, t, J = 7.6,
2
2
2
2
2
3
CH -1′), 2.82 and 3.00 (2H, s, CH -7), 6.25 (1H, s, H-3), 7.94 and 7.96 (1H, 2s, H-5).
2
2
13
C NMR spectrum (100 MHz, DMSO-d , δ, ppm): 191.86 (C-6), 159.99 (C-2), 159.36 (C-10a), 157.29 (C-4),
6
156.77 (C-9a), 121.01 (C-4a), 117.53 (C-5), 114.45 (C-5a), 113.47 (C-3), 111.98 (C-10), 83.60 and 82.19 (C-8), 48.61 and
42.86 (C-7), 33.97 and 33.74 (C-2′′, C-6′′), 33.41 (C-1′), 27.84 (C-4′′), 22.75 (C-3′′), 21.73 (CH -3′′), 21.53 (C-2′, C-5′′),
3
14.31 (C-3′), 8.63 (CH -10).
3
Spiro[(4-butyl-7,8-dihydropyrano[3,2-g]chromen-2,6-dione)-8,1′-(3-methylcyclohexane)] (16). Yield 81%,
mp 155-157°C, C H O .
23 28
4
PMR spectrum (300 MHz, CDCl , δ, ppm, J/Hz): 0.91 (3H, d, J = 7.2, CH -3′′), 0.98 (3H, t, J = 7.2, CH -4′),
3
3
3
1.20-2.15 (13H, CH -2′, CH -3′, CH -2′′, CH -3′′, H-3′′, CH -5′′, CH -6′′), 2.30 and 2.35 (3H, 2s, CH -10), 2.71 and 2.90
2
2
2
2
2
2
3
(2H, s, CH -7), 2.77 (2H, t, J = 7.6, CH -1′), 6.17 (1H, s, H-3), 8.04 and 8.06 (1H, 2s, H-5).
2
2
13
C NMR spectrum (100MHz, DMSO-d , δ, ppm): 191.78 and 191.48 (C-6), 159.94 and 159.93 (C-2), 159.77 and
6
159.33 (C-10a), 157.48 and 156.79 (C-4), 156.73 (C-9a), 120.95 and 120.94 (C-4a), 117.49 and 117.29 (C-5), 114.44 (C-5a),
113.41 (C-3), 111.81 and 111.79 (C-10), 83.60 and 82.17 (C-8), 48.61 and 42.87 (C-7), 33.97 and 33.73 (C-2′′, C-6′′), 31.21
(C-1′), 30.56 (C-2′), 27.82 (C-4′′), 22.56 (C-3′, C-3′′), 21.53 (CH -3′′, C-5′′), 14.34 (C-4′), 8.59 (CH -10).
3
3
155