Helvetica Chimica Acta ± Vol. 84 (2001)
2315
was chromatographed on an Alox II N column (hexane/benzene 4 :1) to give, after evaporation, 569 mg of an
orange oil. It was rechromatographed on an Alox II N column (hexane/benzene 5 :1) to yield, after evaporation,
a yellow oil (377 mg, 44%) of a mixture of three isomers of 151). Final purification was accomplished by semi-
prep. HPLC (Chromasil C8, 10 mm, MeOH/hexane 9 :1) to yield 5.6 mg (95.8% pure by HPLC) of 15. Slightly
yellow, amorphous solid. UV (cyclohexane), 332 (e 68700, A11 1280). 1H-NMR (400 MHz, CDCl3): 6.50
(dd, J 11.2, 15.2, H C(11), H C(11')); 6.27 (d, J 15.2, H C(12), H C(12')); 6.11 (s, H C(7), H C(7'),
H
C(8), H C(8')); 6.08 (d, J 11.2, H C(10), H C(10')); 5.50 ± 5.55 (m, H C(14), H C(14')); 2.26
C(15), C(15')); 1.99 ± 2.03 (m, 2 H C(4), 2 H C(4')); 1.94 (s, 3 H C(19),
(2d, J 3.6, 3.6,
H
H
3 H C(19')); 1.81 (s, 3 H C(20), 3 H C(20')); 1.71 (s, 3 H C(18), 3 H C(18')); 1.60 ± 1.62 (m, 2 H C(3),
2 H C(3')); 1.47 (dd, J 6.0, 2.8, 2 H C(2), 2 H C(2')); 1.02 (s, 3H C(16), 3 H C(16'), 3 H C(17),
3 H C(17')). EI-MS: 538.6 (6, M ), 378.4 (6), 270.2 (20), 269.2 (100, M2), 145.0 (8), 119.0 (15), 95.1 (16), 93.1
(13), 82.1 (15), 69.2 (10).
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Received March 9, 2001
1
)
The lmax of the different isomers, determined by a diode-array UV detector, were 334 for the (all-E)-, 328
for the (11Z)-, and 321 nm for the (11Z,11'Z)-15,15'-dihydro-b,b-carotene.