4
Tetrahedron Letters
J. J. Org. Lett. 2009, 11, 5046-5049. 16. Yadav, J.S.;
(m, 1 H), 3.39 (s, 3 H),2.91-2.68 (m, 6 H), 2.25 (dd, J =
15.2, 7.0 Hz, 1 H), 2.1 (dd, J = 15.4, 3.0 Hz, 1 H),
1.98- 1.89 (m, 3 H), 1.51, 1.48 (q, J = 4.4, 2.4 Hz, 1 H),
1.2 (d, J = 6.1 Hz, 3 H); (13C NMR (75 MHz, CDCl3):
δ = 133.1, 118.5, 77.3, 65.1, 56.4, 51.7, 43.6, 42.8, 41.4,
26.1, 26.0, 24.9, 23.7; IR (KBr): max = 3429, 2927,
1643, 1219, 772 cm-1; HRMS (ESI): calcd. for
C13H24NaO2S2 [M + Na]+ 299.1110; found 299.1106.
Compound 4: Colorless oil; [α]D25= +3.73 (c = 1.0,
Reddy. C.S. Org. Lett. 2009, 11, 1705-1709; (b)
Miyaoka, H.; Yamanishi, M.; Hoshino, A.; Kinbara, A.
Tetrahedron 2006, 62, 4103-4109.
17. (a) Nicolaou, K. C.; Sun, Y.P; Guduru, R.; Banerji, B.;
Chen, D.Y.K.; J. Am. Chem. Soc. 2008, 130, 3633-
3644; (b) Fuwa, H.; Saito, A.; Sasaki, M.; Angew.
Chem. 2010, 122, 3105, Angew. Chem. Int. Ed. 2010,
49, 3041–3044); (c) Inanaga, J.; Hirata, K.; Sacki, H.;
Hatsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn.
1979, 52, 1989-1993.
18. (a) Chandrasekhar, S.; Balaji, S. V.; Rajesh, G.
Tetrahedron Lett. 2010, 51, 5164-5166; (b) Grubbs, R.
H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28,
446-452; (c) Prunet, J. Angew. Chem., Int. Ed. 2003,
42, 2826-2830; (c) Mohapatra, D. K.; Ramesh, K. D.;
Giardello, M. A.; Chorghade, M. S.; Gurjara, M. K.;
Grubbs, R. H. Tetrahedron Lett. 2007, 48, 2621-2625;
(d) Liu, J.; Zhang, L.; He, J.; He, L.; Ma, B.; Pan, X.;
She, X. Tetrahedron: Asymmetry 2008, 19, 906 -911;
(e) Giri, A. G.; Mondal, M.A.; Puranik, V.G.;
Ramana, C.V. Org. Biomol. Chem. 2010, 8, 398-406.
19. (a) Garbaccio, R.M.; Stachel, S.J.; Baeschlin, D.K.;
Danishefsky. S.J. J. Am. Chem. Soc. 2001, 123, 10903-
10908; (b) Ghosh, A.K.; Anderson, D.D. Org. Lett.
2012, 14, 4730-4733.
1
CHCl3); H NMR (300 MHz, CDCl3): δ = 5.86 (ddd, J
= 16.8, 10.3, 6.2 Hz, 1 H), 5.26 (dt, J = 17.0, 1.3 Hz, 1
H), 5.12, 5.11 (dt, J = 10.3, 1.2 Hz, 1 H), 4.58 (q, J =
6.7 Hz, 1 H), 2.56 (dd, J = 6.8, 4.4 Hz, 2 H), 0.89 (s, 9
H); 0.08 (s, 3 H), 0.07 (s, 3 H); 13C NMR (75 MHz,
CDCl3): δ = 176.8, 139.6, 115.1, 70.5, 43.2, 25.6 (3 C),
18.0, -4.4, -5.2; IR (KBr): max = 2928, 2876, 1716,
1460, 1092, 773 cm-1;
Na]+.
MS (ESI): m/z = 253 [M +
Compound 2: Colorless liquid; [α]D25= -1.3 (c = 1.0,
CHCl3); 1H NMR (300 MHz, CDCl3): δ = 5.98-5.83 (m,
2 H), 5.27-5.22 (m, 1 H), 5.18-5.16 (bs, 1 H), 5.15-5.12
(m, 1 H), 5.1-5.06 (m, 1 H), 5.04-4.98 (m, 1 H), 4.59 (q,
J = 13.1, 6.2 Hz, 1 H), 3.58-3.52 (m, 1 H), 3.32 (s, 3 H),
2.90-2.81 (m, 3 H), 2.79, 2.68 (m, 3 H), 2.56 (dd, J =
14.8, 7.0 Hz, 1 H), 2.46 (dd, J = 14.8, 6.2 Hz, 1 H), 2.1
(dd, J = 15.4, 6.4 Hz, 1 H), 2.0-1.93 (m, 2 H), 1.89-1.82
(m, 1 H), 1.73-1.66 (m, 2 H), 1.26 (d, J = 6.2 Hz, 3 H)
0.88 (s, 9 H); 0.07 (s, 3 H), 0.05 (s, 3 H); 13C NMR (75
MHz, CDCl3): δ = 170.3, 140.2, 133.2, 118.3, 114.6,
75.1, 70.5, 68.5, 56.7, 51.3, 44.0, 43.8, 43.5, 42.2,
26.15, 26.11, 25.7 (3 C), 24.9, 20.5, 18.1, -4.4, -4.9; IR
(KBr): max = 2929, 1733, 1219, 802, 772 cm-1; HRMS
(ESI): calcd. for C24H44NaO4S2Si [M + Na] + 511.2342;
found 511.2381.
20. (a) Wang, X.; Wang, W.; Zheng, H.; Su, Y.; Jiang, T.;
He, Y.; She, X. Org. Lett. 2009, 11, 3136-3138; (b) Wu,
Y.; Sun, Y.P. J. Org. Chem. 2006, 71, 5748-5751.
21. Spectroscopic data for representative examples:
Compound 13: Colorless oil; [α]D25= -3.36 (c = 1.6,
CHCl3); 1H NMR (300 MHz, CDCl3): δ = 5.96-5.86 (m,
1 H), 5.18-5.17 (m, 1 H), 5.16-5.14 (m, 1 H), 4.28-4.22
(m, 1 H), 4.15-4.09 (m, 1 H), 3.59-3.56 (bs, 1 H), 3.0-
2.96 (m, 1 H), 2.91-2.76 (m, 4 H), 2.73-2.67 (m, 1 H),
2.28-2.21 (m, 1 H), 2.05-1.98 (m, 1 H), 1.97-1.91 (m, 1
H), 1.89, 1.86 (d, J = 1.8 Hz, 1 H), 1.64-1.58 (m. 1 H),
1.45-1.39 (m, 1 H), 1.18 (d, J = 6.2 Hz, 3 H), 0.9 (s, 9
H), 0.1 (s, 3 H), 0.08 (s, 3 H); 13C NMR (75 MHz,
CDCl3): δ = 132.5, 118.8, 65.7, 65.0, 51.5, 46.6, 45.3,
43.9, 26.3, 26.0, 25.8 (3 C), 24.8, 23.8, 17.9, -4.4, -4.9;
IR (KBr): ν˜ = 3478, 2956, 1741, 1649, 1255, 836 cm-1;
MS (ESI): m/z = 399 [M + Na]+.
Compound 19: Colorless oil; [α]D25= -8.6 (c = 1.0,
CHCl3); 1H NMR (300 MHz, CDCl3): δ = 5.96-5.86 (m,
2 H), 5.35-5.32 (t, J = 1.5, Hz, 1 H), 5.18-5.15 (m, 3
H), 5.14-5.12 (m, 1 H), 4.58-4.54 (m, 1 H), 3.6-3.55 (m,
1 H) 3.33 (s, 3 H), 3.14-3.1 (bs, 1 H, OH), 2.93- 2.85
(m, 2 H), 2.82-2.69 (m, 5 H), 2.63-2.57 (m, 1 H), 2.56-
2.5 (m, 1 H), 2.11 (dd, J = 15.4, 6.0 Hz, 1 H), 1.99-1.91
(m, 3 H), 1.72-1.65 (m, 1 H), 1.25 (d, J = 6.2 Hz, 3 H);
13C NMR (75 MHz, CDCl3): δ = 171.6, 138.8, 133.2,
118.4, 115.2, 75.0, 68.8 (2 C), 56.7, 51.3, 43.8, 43.5,
Compound 14: Colorless liquid; [α]D25= -8.22 (c =
1
0.45, CHCl3); H NMR (300 MHz, CDCl3): δ = 5.99-
41.6, 42.2, 26.12, 26.09, 24.8, 20.6; IR (KBr): max
=
2959, 2919, 2851, 1728, 1219, 802, 772 cm-1; HRMS
(ESI): calcd. for C18H30NaO4S2 [M + Na]+ 397.1478;
found 397.1514.
5.87 (m, 1 H), 5.18-5.16 (bs, 1 H), 5.15-5.12 (m, 1 H),
3.99-3.91 (m, 1 H), 3.72-3.65 (m, 1 H), 3.35 (s, 3 H),
2.90-2.68 (m, 6 H), 2.15, 2.12 (d, J = 5.8 Hz, 1 H),
1.98-1.87 (m, 3 H), 1.71-1.59 (m, 2 H), 1.17 (d, J = 6.1
Hz, 3 H), 0.9 (s, 9 H); 0.09 (s, 3 H), 0.08 (s, 3 H); 13C
NMR (75 MHz, CDCl3): δ = 113.3, 118.2, 74.9, 65.5,
56.0, 51.5, 46.5, 43.6, 43.3, 26.19, 26.16, 25.9 (3 C),
24.9, 24.3, 18.0, -3.9, -4.6; IR (KBr): max = 2959,
2855, 1742, 1260, 802, 773 cm-1; MS (ESI): m/z = 413
[M + Na]+.
Compound 20: Light brown oil; [α]D25= -12.36 (c =
1
0.55, CHCl3); H NMR (300 MHz, CDCl3): δ = 5.89-
5.81 (m, 1 H), 5.62-5.56 (m, 1 H), 5.22-5.15 (m, 1 H),
4.57-4.51 (m, 1 H), 3.51-3.44 (m, 1 H) 3.33 (s, 3 H),
2.98- 2.89 (m, 3 H), 2.80-2.70 (m, 3 H), 2.65-2.63 (m, 2
H), 2.12-2.01 (m, 2 H), 1.99-1.84 (m, 3 H), 1.69-1.63
(m, 1 H), 1.24 (d, J = 6.2 Hz, 3 H); 13C NMR (75 MHz,
CDCl3): δ = 171.6, 134.9, 127.3, 76.1, 70.0, 68.9, 56.5,
50.7, 45.2, 42.3, 41.8, 41.3, 26.4 (2 C), 25.1, 21.1; IR
(KBr): max = 3432, 2980, 2911, 2829, 1721, 1276,
Compound 3: Colorless liquid; [α]D25= -12.7 (c = 0.85,
CHCl3); 1H NMR (300 MHz, CDCl3): δ = 5.98-5.87 (m,
1 H), 5.18-5.11 (m, 2 H), 4.17-4.10 (m, 1 H), 3.85-3.8