V. Singh, S. Q. Alam / Bioorg. Med. Chem. Lett. 10 (2000) 2517±2519
2519
Scheme 3.
7. (a) Adler, E.; Holmberg, K. Acta. Chem. Scand. 1974, 28B,
465. (b) Singh, V.; Bedekar, A. V.; Caira, M. R. J. Chem. Res.
(S) 1995, 452.
Acknowledgements
ꢁ
8. Data for 3: mp 76±77 C; IR (®lm) nmax: 1707 cm 1; UV
We thank RSIC, I.I.T. Bombay for spectral facilities.
S. Q. Alam is thankful to I.I.T. Bombay for a teaching
assistantship. Financial support from BRNS is grate-
fully acknowledged.
1
lmax (MeOH): 218, 289 nm; H NMR (300 MHz, CDCl3): d
5.49 (m, 1H), 4.21 (part of an AB system, JAB=9 Hz, 1H),
4.01 (superimposed dd, J1=J2=7.5 Hz, 1H), 3.90 (part of an
AB system, JAB=9 Hz, 1H), 3.20 (dd, J1=12 Hz, J2=7.5 Hz,
1H), 2.8 (m, 1H), 2.50 (complex m, 1H), 2.12 (m of part of an
AB system, JAB=12 Hz, 1H), 2.08 (m of part of an AB sys-
tem, JAB=12 Hz, 1H), 1.98±1.92 (m, 1H), 1.90 (d, J=1.5 Hz,
3H), 1.24 (dd, J1=12.5 Hz, J2=6.5 Hz, 1H); 13C NMR (75
MHz, CDCl3): d 208.2, 148.4, 121.2, 71.5, 69.0, 60.9, 42.5,
39.4, 38.1, 26.6, 19.6; Mass (m/z): 178 (M+), 136
[M+ (CH2CO)]. Anal. Found: C, 73.99; H, 7.81%. Calcd:
C, 74.15; H, 7.86% for C11H14O2.
References and Notes
1. (a) Mehta, G.; Srikrishna, A. Chem. Rev., 1997, 97, 671 and
references cited therein. (b) Little, R. D. Chem. Rev. 1996, 96,
93. (c) Singh, V.; Thomas, B. Tetrahedron 1998, 54, 3647.
(d) Paquette, L. A. Top. Curr. Chem. 1984, 119, 1.
2. (a) Masuya, K.; Domon, K.; Tanino, K.; Kuwajima, I. J.
Am. Chem. Soc. 1998, 120, 1724. (b) Lautens, M.; Blackwell, J.
Synthesis 1998, 537. (c) Krishnamurthy, V.; Rawal, V. H. J.
Braz. Chem. Soc. 1998, 9, 341.
9. (a) Corey, E. J.; Cheng, X.-M. The Logic of Chemical
Synthesis; John Wiley & Sons: New York, 1989. (b) Chanon,
M.; Barone, R.; Baralotto, C.; Julliard, M.; Hendrickson, J. B.
Synthesis 1998, 1559.
10. (a) Data for 4: mp 57±59 ꢁC; IR: 1726 cm
3. (a) Toyota, M.; Nishikawa, Y.; Motoki, K.; Yoshida, N.;
Fukumoto, K. Tetrahedron 1993, 49, 11189. (b) Fukumoto,
K.; Toyoda, S. Jpn. Patent 1995 95, 179, 449; Chem. Abstr.
1995, 123, 257083d. (c) Amey, D. M.; Blakemore, D. C.;
Drew, M. G. B.; Gilbert, A.; Heath, P. J. Photochem. Photo-
biol. A: Chem. 1997, 102, 173.
4. (a) Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96,
3065 and references cited therein. (b) Katayama, S.; Hir-
amatsu, H.; Aoe, K.; Yamaguchi, K. J. Chem. Soc., Perkin
Trans. 1 1997, 561. (c) Singh, V.; Porinchu, M. Tetrahedron
1996, 52, 7087. (d) Uyehara, T.; Murayama, T.; Sakai, K.;
Ueno, M.; Sato, T. Tetrahedron Lett. 1996, 37, 7295.
5. (a) Strunz, G. M.; Bethell, R.; Dumas, M. T.; Boyonoski,
N. Can. J. Chem. 1997, 75, 742. (b) Sterner, O.; Anke, T.;
Sheldrick, W. S.; Steglich, W. Tetrahedron 1990, 46, 2389.
(c) Murata, Y.; Ohtsuka, T.; Shirahama, H.; Matsumoto, T.
Tetrahedron Lett. 1981, 22, 4313. (d) Ayer, W. A.; Saeedi-
Ghomi, M. H.; Van Engen, D.; Tagle, B.; Clardy, J. Tetra-
hedron 1981, 37, 279.
1
;
1H NMR
(300 MHz, CDCl3): d 3.90 (d of part of an AB system,
JAB=9.5 Hz, J2=7 Hz, 1H), 3.78 (d of part of an AB system,
JAB=9.5 Hz, J2=2.5 Hz, 1H), 3.70 (part of an AB system,
JAB=9.5 Hz, 1H), 3.62 (part of an AB system, JAB=9.5 Hz,
1H), 2.76±2.54 (m, 3H), 1.92±1.84 (m, 4H), 1.40 (s, 3H); 13C
NMR (75 MHz, CDCl3): d 214.6, 73.5, 67.2, 51.0, 46.0, 45.7,
45.1, 44.2, 43.2, 13.2 (one `C' not observed). Anal. Found: C,
74.17; H, 7.93%. Calcd: C, 74.15; H, 7.86% for C11H14O2.
(b) Data for 5: mp 39±40 ꢁC; IR: 1778 cm 1; UV lmax
1
(MeOH): 217, 289 nm; H NMR (300 MHz, CDCl3): d 5.34
(br m, 1H), 4.49 (m of d, J=13 Hz, 1H), 4.35±4.27 (over-
lapped m, 2H), 3.34 (dd, J1=10.5 Hz, J2=7.5 Hz, 1H), 3.0 (d
of part of an AB system, JAB=17 Hz, J2=8.5 Hz, 1H), 2.80
(part of an AB system, JAB=17 Hz, J2=8.5 Hz, 1H), 2.60 (m,
1H), 2.44 (m, 1H), 2.04 (d of dd, J1=12.5 Hz, J2=6 Hz,
J3=2.5 Hz, 1H), 1.32 (s, 3H, CH3), 1.12 (ddd, J1=ꢀ12 Hz,
J2=8.5 Hz, J3=4 Hz, 1H); 13C NMR (75 MHz, CDCl3): d
209.7 (CO), 143.5, 115.9, 73.7, 70.2, 63.0, 46.0, 34.8, 31.2, 22.8,
20.5. Mass (m/z): 178 (M+).
6. (a) Singh, V. Acc. Chem. Res. 1999, 32, 324. (b) Singh, V.;
Prathap, S.; Porinchu, M. J. Org. Chem. 1998, 63, 4011.