BULLETIN OF THE
Note
KOREAN CHEMICAL SOCIETY
was filtered through Celite. The solvent was then removed,
and the residue was purified by column chromatography (sil-
ica gel, 33% ethyl acetate in hexane) to give aldehyde 7 (1.1 g,
organic layer was washed with saturated NaHCO solution,
3
water, and brine, and then evaporated in-vacuo. The residue
was purified by column chromatography (silica gel, 25% ethyl
acetate in hexane)to afford target molecule 1(0.45 g, 91%). IR
7
1
0%). IR (KBr) 3016, 2937, 2859, 2732, 1693, 1637, 1136,
–
1
1
–1
077, 1033 cm ; H NMR (CDCl , 500 MHz) δ 9.50 (d, J
(KBr) 3017, 2962, 2931, 2856, 1741, 1461, 1239, 1037 cm ;
3
1
=
8.0 Hz, 1H), 6.85 (dt, J = 15.5, 7.0 Hz, 1H), 6.12 (dd, J =
H NMR (CDCl , 500 MHz) δ 6.33–6.27 (m, 1H), 5.91 (t, J =
3
1
3
2
1
1
3
5.5, 8.0 Hz, 1H), 4.59–4.56 (m, 1H), 3.89–3.84 (m, 1H),
.76–3.70 (m, 1H), 3.53–3.48 (m, 1H), 3.42–3.36 (m, 1H),
.37–2.32 (m, 2H), 1.86–1.80 (m, 1H), 1.75–1.69 (m, 1H),
.64–1.47 (m, 8H), 1.43–1.33 (m, 4H); C NMR (CDCl3,
25 MHz) δ 194.1, 158.9, 133.0, 98.9, 67.5, 62.4, 60.2,
2.7, 30.8, 29.6, 29.0, 26.0, 25.5, 19.7.
11.0 Hz, 1H), 5.64 (dt, J = 15.0, 7.0 Hz, 1H), 5.33–5.28 (m,
1H), 4.05 (t, J = 7.0 Hz, 2H), 2.22–2.15 (m, 2H), 2.12–2.06
(m, 2H), 2.04 (s, 3H), 1.65–1.59 (m, 2H), 1.44–1.31 (m,
1
3
13
6H), 0.99 (t, J = 7.5 Hz, 3H); C NMR (CDCl , 125 MHz)
3
δ 171.2, 134.4, 131.8, 128.0, 125.7, 64.6, 32.8, 29.3, 28.8,
28.6, 25.8, 21.0(2), 14.3.
(7E,9Z)-Dodecadien-1-ol (8): To a suspension of propyl-
triphenylphosphonium bromide (1.43 g, 4.0 mmol) in dry
THF (30 mL) was added tert-BuOK (5.75 mL, 5.75 mmol)
and the reaction mixture was stirred for 30 min at room tem-
perature. Aldehyde 7 (0.8 g, 3.3 mmol) in dry THF (10 mL)
was then added dropwise. After stirring for 1 h at room tem-
perature, the reaction was quenched with water and the solvent
was removed in-vacuo. The residue was then extracted with
water and ether. After the solvent was removed, the residue
was purified by column chromatography (silica gel, 33% ethyl
acetate in hexane) to give the Z-coupling product (0.66 g,
Acknowledgment. This work was supported by the research
fund of Andong National University 2012.
References
1
. (a)R. Ideses, J. T. Klug, A. Shani, S. Gothilf, E. Gurevitz, J. Chem.
Ecol. 1982, 8, 195; (b) P. Witzgall, M. Tasin, H.-R. Buser,
G. Wergner-Kib, V. M. Mancerbon, C. Ioriatti, A.-C. Backman,
M. Bengtsson, L. Lehmann, W. Francke, J. Chem. Ecol. 2005,
3
1, 2923.
7
5%). The product (0.66 g, 2.5 mmol) was then deprotected
2
. W. Roelofs, J. Kochansky, R. Carde, H. Arn, S. Rauscher, Ento-
mon. Ges. 1973, 46, 71.
ꢀ
with PPTS (0.056 g, 0.22 mmol) at 80 C in EtOH (20 mL)
to give alcohol 8 (0.4 g, 88%) after purification (silica gel,
3. R. Roehrich, J. P. Carles, C. Tresor, M. De Vathaire, Ann. Zool.
Ecol. Anim. 1979, 11, 659.
4. (a) H. J. Bestmamm, J. Sub, O. Vostrowsky, Tetrahedron Lett.
3
2
3% ethyl acetate in hexane). IR (KBr) 3330, 3017, 2961,
–1 1
930, 2855, 1461, 1057 cm ; H NMR (CDCl 500 MHz)
3
,
1
979, 20, 2467; (b) V. Ratovelomanana, G. Linstrumelle,
δ 6.33–6.27 (m, 1H), 5.91 (t, J = 10.5 Hz, 1H), 5.65 (dt, J =
5.0, 7.5 Hz, 1H), 5.65 (dt, J = 10.5, 7.5 Hz, 1H), 3.64 (t, J
7.0 Hz, 2H), 2.21–2.15 (m, 2H), 2.12–2.05 (m, 2H),
.60–1.54 (m, 2H), 1.44–1.31 (m, 6H), 0.99 (t, J = 7.5 Hz,
Tetrahedron Lett. 1981, 22, 315; (c) R. Rossi, A. Carpita, G. Quir-
ici, Tetrahedron 1981, 37, 2617; (d) G. Gassani, P. Massardo,
P. Piccardi, Tetrahedron Lett. 1983, 24, 2513; (e) I. Ujvary,
A. Kis-Tamas, L. Novak, J. Chem. Ecol. 1985, 11, 113; (f ) Z.
G. Chrelashvili, M. V. Mavrov, A. V. Dolidze, A. O. Chizhov,
E. P. Serebryakov, Russ. Chem. Bull. 1993, 42, 1090.
1
=
1
3
1
1
3
H); C NMR (CDCl3, 125 MHz) δ 134.5, 131.8, 128.0,
25.6, 63.0, 32.8, 29.4, 28.8, 25.6, 21.0, 19.7, 14.3.
(7E,9Z)-Dodecadienyl acetate (1): To a solution of alco-
5
. W. S. Wadsworth, W. D. Emmons Jr.. , J. Am. Chem. Soc. 1961,
hol 8 (0.4 g, 2.2 mmol) in pyridine (2.0 mL) was added acetic
8
3, 1733.
ꢀ
anhydride (0.62 mL, 6.6 mmol) at 0 C and the reaction mix-
6. (a) A. E. Finholt, A. C. Bond, H. I. Schlesinger, J. Am. Chem. Soc.
1947, 69, 1199; (b) H. C. Brown, N. M. Yoon, J. Am. Chem. Soc.
1966, 88, 1464.
ture was stirred for 3 h at room temperature. The reaction mix-
ture was diluted with ice water and extracted with ether. The
Bull. Korean Chem. Soc. 2015, Vol. 36, 421–423
© 2015 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.bkcs.wiley-vch.de
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