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G. Mehta, M. K. Bera / Tetrahedron Letters 50 (2009) 3519–3522
2. Selected references: Early work, (a) Karanjgoakar, C. G.; Rama Rao, A. V.;
Venkataraman, K.; Palmer, K. J. Tetrahedron Lett. 1973, 14, 4977–4980; (b)
Baystrov, N. S.; Chernov, B. K.; Dobrynin, V. N.; Kolosov, M. N. Tetrahedron Lett.
212.73, 132.62, 131.65, 124.19, 123.34, 52.51, 42.72, 41.37, 40.91, 40.84, 27.45,
27.27, 25.82, 25.66, 21.86, 20.02, 17.88, 17.58; HRMS (ES): m/z calcd for
C18H30
O
(M+Na): 285.2194, found: 285.2189. 16: IR (neat): mmax 1741,
;
1975, 16, 2791–2794; More recently, (c) Šavikin-Fodulovic´, K.; Aljancic, I.; Vajs,
1704 cmÀ1
1H NMR (400 MHz, CDCl3): d 5.11–5.02 (m, 3H), 3.65 (s, 3H),
ˇ ´
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2.54 (1/2ABq, J = 10.5 Hz, 1H), 2.27–2.12 (m, 6H), 1.98–1.89 (m, 6H), 1.72 (s,
3H), 1.70 (s, 3H), 1.68 (s, 3H), 1.61 (s, 3H), 1.59 (s, 6H), 1.44–1.38 (m, 4H), 0.73
(s, 3H); 13C NMR (100 MHz, CDCl3): d 215.36, 173.82, 134.31, 132.57, 131.61,
124.22, 123.20, 119.32, 51.68, 50.96, 49.97, 41.22, 41.05, 38.93, 38.29, 32.14,
31.03, 28.69, 27.81, 26.04, 25.86, 25.67, 22.01, 19.33, 17.97, 17.91, 17.62;
HRMS (ES): m/z calcd for C27H44O3 (M+Na): 439.3188, found: 439.3185. 19: IR
(neat): mmax 1723, 1700 cmÀ1 1H NMR (400 MHz, CDCl3): d 5.22–5.18 (m, 1H),
;
5.07–5.03 (m, 2H), 3.19 (s, 1H), 2.75–2.68 (m, 1H), 2.57–2.55 (m, 1H), 2.26–
2.08 (m, 6H), 1.95–1.81 (m, 3H), 1.73 (s, 3H), 1.71 (s, 3H), 1.67 (s, 3H), 1.64 (s,
3H), 1.62 (s, 3H), 1.58 (s, 3H), 1.31–1.16 (m, 2H), 0.91–0.80 (m, 2H), 0.83 (s,
3H); 13C NMR (100 MHz, CDCl3): d 210.87, 208.12, 134.50, 133.08, 131.91,
123.97, 122.71, 119.35, 75.10, 49.18, 48.47, 42.71, 42.62, 39.75, 38.86, 35.37,
29.76, 29.46, 26.04, 25.85, 25.69, 22.67, 21.48, 18.19, 17.93, 17.59; HRMS (ES):
m/z calcd for C26H40O2 (M+Na): 407.2926, found: 407.2922. 6: IR (neat): mmax
1724, 1696 cmÀ1 1H NMR (400 MHz, CDCl3): d 5.22–5.18 (m, 1H), 5.08–5.01
;
(m, 3H), 3.22 (s, 1H), 2.73–2.69 (m, 1H), 2.51–2.49 (m, 1H), 2.24–2.02 (m, 7H),
1.88–1.84 (m, 2H), 1.73 (s, 6H), 1.69 (s, 3H), 1.67 (s, 3H), 1.63 (s, 3H), 1.58 (s,
6H), 1.57 (s, 3H), 1.31–1.12 (m, 3H), 0.89–0.79 (m, 2H), 0.82 (s, 3H); 13C NMR
(100 MHz, CDCl3): d 210.62, 208.11, 134.38, 133.90, 133.00, 131.95, 123.98,
122.79, 120.94, 119.53, 75.64, 50.25, 48.84, 48.26, 42.52, 42.46, 38.93, 37.09,
35.47, 29.81, 29.25, 27.83, 26.06, 25.89, 25.85, 25.69, 21.42, 18.45, 17.97,
17.91, 17.61; HRMS (ES): m/z calcd for C31H48O2 (M+Na): 475.3552, found:
3. For
a recent review on the bioactivity of hyperforin, see: Medina, M. A.;
Martinez-Poveda, B.; Amores-Sanchez, M. I.; Quesada, A. R. Life. Sci. 2006, 79,
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Shimizu, Y.; Kuramochi, A.; Usuda, H.; Kanai, M.; Shibasaki, M. Tetrahedron Lett.
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4877 and references cited therein.
475.3549. 21: IR (neat): mmax 1717 cmÀ1 1H NMR (300 MHz, CDCl3): d 5.15–
;
5.05 (m, 2H), 2.52–2.19 (m, 4H), 2.07–1.79 (m, 7H), 1.72 (s, 3H), 1.68 (s, 3H),
1.62 (s, 3H), 1.60 (s, 3H), 1.30–1.11 (m, 2H), 1.04 (s, 3H); 13C NMR (75 MHz,
CDCl3): d 212.27, 132.60, 131.63, 124.38, 123.60, 51.80, 46.07, 40.99, 40.09,
34.35, 26.98, 26.57, 26.20, 25.81, 25.66, 21.79, 17.85, 17.52; HRMS (ES): m/z
calcd for C18H30
O
(M+Na): 285.2194, found: 285.2191. 23: IR (neat): mmax
1741, 1703 cmÀ1
;
1H NMR (400 MHz, CDCl3): d 5.09–5.02 (m, 3H), 3.65 (s, 3H),
2.28–2.11 (m, 7H), 1.97–1.90 (m, 2H), 1.81–1.61 (m, 4H), 1.72 (s, 3H), 1.69 (s,
3H), 1.67 (s, 3H), 1.59 (s, 9H), 1.51–1.44 (m, 2H), 1.10–1.06 (m, 2H), 1.03 (s,
3H); 13C NMR (100 MHz, CDCl3): d 214.80, 173.88, 134.27, 132.53, 131.68,
124.44, 123.62, 119.43, 51.68, 50.92, 49.48, 44.15, 41.20, 38.27, 32.22, 32.06,
31.35, 28.73, 27.86, 26.31, 26.00, 25.85, 25.68, 21.72, 17.99, 17.88, 17.49;
HRMS (ES): m/z calcd for C27H44O3 (M+Na): 439.3188, found: 439.3189. 26: IR
(neat): mmax 1724, 1699 cmÀ1 1H NMR (400 MHz, CDCl3): d 5.21–5.18 (m, 1H),
;
6. (a) Mehta, G.; Bera, M. K. Tetrahedron Lett. 2006, 47, 689–692; (b) Mehta, G.;
Bera, M. K.; Chatterjee, S. Tetrahedron Lett. 2008, 49, 1121–1124; See also:
Usuda, H.; Kanai, M.; Shibasaki, M. Org. Lett. 2002, 4, 859–862.
5.08–5.04 (m, 2H), 3.22 (s, 1H), 2.73–2.66 (m, 1H), 2.57–2.53 (m, 1H), 2.22–
2.03 (m, 7H), 1.99–1.92 (m, 1H), 1.85–1.79 (m, 3H), 1.72 (s, 6H), 1.68 (s, 3H),
1.62 (s, 3H), 1.60 (s, 3H), 1.57 (s, 3H), 1.20–1.12 (m, 2H), 1.07 (s, 3H); 13C NMR
(100 MHz, CDCl3): d 210.84, 209.25, 134.46, 133.07, 132.22, 123.79, 122.95,
119.34, 73.92, 48.96, 48.09, 44.21, 42.17, 39.58, 35.26, 32.81, 29.89, 28.92,
26.06, 25.86, 25.69, 23.62, 21.23, 17.93, 17.89, 17.53; HRMS (ES): m/z calcd for
C26H40O2 (M+Na): 407.2926, found: 407.2926.
7. All new compounds were fully characterized on the basis of their IR, 1H NMR,
13C NMR and mass spectral data. Selected spectral data for key compounds: 9:
IR (neat): mmax 1715 cmÀ1 1H NMR (300 MHz, CDCl3): d 5.13–5.06 (m, 2H),
;
2.38–2.19 (m, 5H), 2.07–1.87 (m, 4H), 1.72 (s, 3H), 1.69 (s, 3H), 1.61 (s, 6H),
1.56–1.41 (m, 2H), 1.34–1.22 (m, 2H), 0.82 (s, 3H); 13C NMR (75 MHz, CDCl3): d
8. Gheorghe, A.; Schulte, M.; Reiser, O. J. Org. Chem. 2006, 71, 2173–2177.