P. R. Krishna, R. R. Kadiyala / Tetrahedron Letters 51 (2010) 4981–4983
4983
9. Spectral data for selected compounds: Compound 5: colorless syrup. ½a D25
ꢁ
ꢀ18.0 (c
Acknowledgment
0.51, CHCl3); 1H NMR (300 MHz, CDCl3): d 6.17 (s, 1H), 5.78 (s, 1H), 4.57 (q, 1H,
J = 6.4, 12.8 Hz), 4.20 (q, 2H, J = 6.9, 7.1 Hz), 1.38–1.31 (m, 6H). 13C NMR
(75 MHz, CDCl3): d 166.8, 143.4, 123.9, 67.6, 61.2, 21.9, 14.1. ESIMS: m/z 167
One of the authors (R.R.K.) thanks CSIR, New Delhi, for financial
support in the form of a fellowship.
(M+Na)+. IR (neat): 3448, 1622, 1747 cmꢀ1. Compound 12: colorless syrup. ½a 2D5
ꢁ
ꢀ84.0 (c 0.2, CHCl3); 1H NMR (300 MHz, CDCl3): d 5.15 (d, 2H, J = 10.1 Hz), 4.54
(d, 1H, J = 6.7 Hz), 4.51 (d, 1H, J = 6.7 Hz), 4.21 (q, 1H, J = 6.6, 13.2 Hz), 3.84 (d,
1H, J = 11.2 Hz), 3.68 (d, 1H, J = 13.5 Hz), 3.39 (d, 1H, J = 1.9 Hz), 3.38 (s, 3H),
2.95–2.92 (m, 1H), 1.34 (d, 3H, J = 6.6 Hz). 13C NMR (75 MHz, CDCl3): d 146.3,
111.7, 94.7, 73.0, 61.8, 61.0, 56.1, 54.7, 21.6. ESIMS: m/z 211 (M+Na)+. IR (neat):
Supplementary data
3450, 1629 cmꢀ1. Compound 3: colorless syrup. ½a 2D5
ꢁ
+114.0 (c 0.3, CHCl3); 1H
Supplementary data associated with this article can be found, in
NMR (300 MHz, CDCl3): d 5.91–5.77 (m, 1H), 5.25 (d, 1H, J = 10.5 Hz), 5.23 (s,
2H), 5.09 (d, 1H, J = 10.5 Hz), 4.61–4.35 (m, 6H), 4.20 (q, 1H, J = 6.6, 12.8 Hz),
3.39 (s, 3H), 3.33 (s, 3H), 1.81–1.75 (m, 2H), 1.29 (d, 3H, J = 6.4 Hz). 13C NMR
(75 MHz, CDCl3): d 149.4, 140.4, 114.2, 96.0, 93.9, 93.4, 75.2, 72.2, 71.6, 55.8,
55.2, 42.8, 20.6. IR (neat): 3345, 1625 cmꢀ1. ESIMS: m/z 283 (M+Na)+, HRMS m/
z: Calcd for C13H24O5Na: 283.1322. Found: 283.1328. Compound 2: colorless
References and notes
1. Druzhinina, I.; Kubicek, C. P. J. Zhejiang Univ. Sci. 2005, 6B, 100–112.
2. Li, G.-H.; Zheng, L.-I.; Liu, F.-F.; Dang, L.-Z.; Li, L.; Huang, R.; Zhang, K.-Q. Nat.
Prod. Res. 2009, 23, 1431–1435.
3. (a) Radha Krishna, P.; Rachna, S.; Reddy, P. S. Synlett 2008, 2897–2912; (b) Radha
Krishna, P.; Narasingam, M.; Kannan, V. Tetrahedron Lett. 2004, 45, 4773–4775;
(c) Radha Krishna, P.; Narasingam, M. J. Comb. Chem. 2007, 9, 62–69; (d) Radha
Krishna, P.; Reddy, P. S. J. Comb. Chem. 2008, 10, 426–435.
syrup. ½a 2D5
ꢁ
ꢀ46.5 (c 0.35, CHCl3); 1H NMR (300 MHz, CDCl3): d 5.89 (d, 1H,
J = 11.7 Hz), 4.73–4.62 (m, 6H), 4.49–4.42 (m, 1H), 3.39 (s, 3H), 3.38 (s, 3H),
1.76–1.67 (m, 2H), 1.31 (d, 3H, J = 6.4 Hz). 13C NMR (75 MHz, CDCl3): d 131.2,
131.5, 94.6, 95.5, 79.1, 73.9, 69.5, 55.8, 42.2, 21.0. IR (neat): 3552, 1632 cmꢀ1
.
ESIMS: m/z 255 (M+Na)+, HRMS m/z: Calcd for C11H20O5Na: 255.1463. Found:
255.1465. Compound 15: colorless syrup. ½a D25
ꢁ
ꢀ133.1 (c 0.44, CHCl3); 1H NMR
4. Hayashi, N.; Yanagihara, K.; Tsuboi, S. Tetrahedron: Asymmetry 1998, 9, 3825–
3830.
(300 MHz, CDCl3): d 6.21 (s, 1H), 4.82 (br d, 1H, J = 6.0 Hz), 4.75–4.64 (m, 5H),
3.42 (s, 3H), 3.40 (s, 3H), 2.77 (dd, 1H, J = 6.0, 12.0 Hz), 2.41 (dd, 1H, J = 2.2,
15.5 Hz), 1.41 (3H, d, J = 6.7 Hz). 13C NMR (75 MHz, CDCl3): d 204.4, 179.5, 129.8,
96.3, 94.9, 74.1, 69.6, 56.0, 55.4, 43.3, 19.6. IR (neat): 1735, 1620 cmꢀ1. ESIMS:
m/z 253 (M+Na)+, HRMS m/z: Calcd for C11H18O5Na: 253.1139. Found: 253.1134.
5. (a) Martin, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K.
B. J. Am. Chem. Soc. 1981, 103, 6237–6240; (b) Radha Krishna, P.; Kannan, V.;
Ilangovan, A.; Sharma, G. V. M. Tetrahedron: Asymmetry 2001, 12, 829–837.
6. (a) Sharpless, K. B. Janssen Chim. Acta 1988, 6, 3. Chem. Abstr. 1988, 109,
128034a; (b) Wershofen, S.; Scharf, H.-D. Synthesis 1988, 854–857.
7. (a) Garber, B. S.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000,
122, 8168–8179; (b) Gessler, S.; Randi, S.; Blechert, S. Tetrahedron Lett. 2000, 41,
9973–9976; (c) Wang, H.; Matsuhashi, H.; Doan, D. B.; Goodmen, S. N.; Ouyang,
X., ; Clark, W. M., Jr. Tetrahedron 2009, 65, 6291–6303; (d) Radha Krishna, P.;
Kadiyala, R. R. Tetrahedron Lett. 2010, 51, 2586–2588.
Compound 1: solid. Mp 99–101.
½
a 2D5
ꢁ
ꢀ27.5 (c 0.17, CHCl3); 1H NMR
(300 MHz, CDCl3): d 6.09 (s, 1H, H-2), 5.07 (br d, 1H, J = 5.3 Hz, H-4), 4.93
(q, 1H, J = 6.4 Hz, H-6), 2.86 (dd, 1H, J = 6.4, 18.5 Hz, H-5), 2.42 (dd, 1H, J = 1.8,
16.7, Hz, H-5), 1.53 (d, 3H, J = 6.7 Hz, H-7). 13C NMR (75 MHz, CDCl3): d 205.5,
181.5, 129.0, 71.2, 67.0, 45.3, 22.5. IR (neat): 3435, 1742, 1621 cmꢀ1. ESIMS:
m/z 165 (M+Na)+, HRMS m/z: Calcd for C7H10O3Na: 165.1266. Found:
165.1269.
8. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155–4156.